Pyridine compound

ABSTRACT

A pyridine compound represented by formula (I), or an N-oxide thereof is provided, wherein the variable groups are as defined in the specification. The pyridine compound of formula has excellent control effects against harmful arthropods.

CROSS-REFERENCE TO RELATED APPLICATION

This application is a Section 371 of International Application No. PCT/JP2016/080792, filed Oct. 18, 2016, which was published in the Japanese language on Apr. 27, 2017, under International Publication No. WO 2017/069105 A1, which claims priority under 35 U.S.C. § 119(b) to Japanese Application No. 2015-206967, filed Oct. 21, 2015 and, Japanese Application No. 2015-208640, filed Oct. 23, 2015, the disclosures of which are incorporated herein by reference in their entirety.

TECHNICAL FIELD

The present invention relates to a certain class of pyridine compound and its use for controlling harmful arthropods.

BACKGROUND ART

To date, some compounds for controlling harmful arthropods have been developed and come into practical use.

Also, a certain class of heterocyclic compounds has been known (for example, see Patent Document 1).

CITATION LIST Patent Document

Patent Document 1: JP 2000-26421 A

SUMMARY OF THE INVENTION Problems to be Solved by Invention

An object of the present invention is to provide a compound having excellent control efficacies against harmful arthropods.

Means to Solve Problems

The present invention provides the followings.

[1] A compound represented by formula (I)

[wherein:

R¹ represents a C2-C10 chain hydrocarbon group having one or more halogen atoms, a (C1-C5 alkoxy)C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfanyl)C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfinyl)C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfonyl)C2-C5 alkyl group having one or more halogen atoms, a (C3-C7 cycloalkyl)C1-C3 alkyl group having one or more substituents selected from Group G, or a C3-C7 cycloalkyl group having one or more substituents selected from Group G;

R² represents a C1-C6 alkyl group optionally having one or more halogen atoms, a cyclopropylmethyl group, or a cyclopropyl group;

q represents 0, 1, 2, 3, or 4;

R³ represents a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group B, a phenyl group optionally having one or more substituents selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, a OR¹², a NR¹¹R¹², a NR^(11a)R^(12a), a NR²⁹NR¹¹R¹², a NR²⁹OR¹¹, a NR¹¹C(O)R¹³, a NR²⁹NR¹¹C(O)R¹³, a NR¹¹C(O)OR¹⁴, a NR²⁹NR¹¹C(O)OR¹⁴, a NR¹¹C(O)NR¹⁵R¹⁶, a NR²⁴NR¹¹C(O)NR¹⁵R¹⁶, a N═CHNR¹⁵R¹⁶, a N═S(O)_(x)R¹⁵R¹⁶, a S(O)_(y)R¹⁵, a SF₅, a C(O)OR¹⁷, a C(O)NR¹¹R¹², a cyano group, a nitro group, or a halogen atom, wherein when q represents 2 or 3, two or three R³ may be identical to or different from each other;

p represents 0, 1, 2, or 3;

R⁶ represents a C1-C6 alkyl group optionally having one or more halogen atoms, a OR¹⁸, a NR¹⁸R¹⁹, a cyano group, a nitro group, or a halogen atom, wherein when p represents 2, two R⁶ may be identical to or different from each other;

R¹¹, R¹⁷, R¹⁸, R¹⁹, R²⁴, and R²⁹ represent each independently a hydrogen atom or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

R¹² represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkyl group having one substituent selected from Group F, or a S(O)₂R²³;

R²³ represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or a phenyl group optionally having one or more substituents selected from Group D;

R^(11a) and R^(12a) are combined with the nitrogen atom to which they are attached to represent a 3-7 membered nonaromatic heterocyclic group optionally having one or more substituents selected from Group E {wherein said 3-7 membered nonaromatic heterocyclic group represents an aziridine ring, an azetidine ring, a pyrrolidine ring, an imidazoline ring, an imidazolidine ring, a piperidine ring, a tetrahydropyrimidine ring, a hexahydropyrimidine ring, a piperazine ring, an azepane ring, an oxazolidine ring, an isoxazolidine ring, a 1,3-oxazinane ring, a morpholine ring, a 1,4-oxazepane ring, a thiazolidine ring, an isothiazolidine ring, a 1,3-thiazinane ring, a thiomorpholine ring, or a 1,4-thiazepane ring};

R¹³ represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally having one or more halogen atoms, a phenyl group optionally having one or more substituents selected from Group D, or a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituents selected from Group D;

R¹⁴ represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally having one or more halogen atoms, or a phenyl C1-C3 alkyl group {wherein the phenyl moiety in the phenyl C1-C3 alkyl group may optionally have one or more substituents selected from Group D};

R¹⁵ and R¹⁶ represent each independently a C1-C6 alkyl group optionally having one or more halogen atoms;

n and y represent each independently 0, 1, or 2;

x represents 0 or 1;

Group B: a group consisting of a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, a cyano group, a hydroxy group, and a halogen atom;

Group C: a group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, and a halogen atom;

Group D: a group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a hydroxy group, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, a sulfanyl group, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, an amino group, a NHR²¹, a NR²¹R²², a C(O)R²¹ group, a OC(O)R²¹ group, a C(O)OR²¹ group, a cyano group, a nitro group, and a halogen atom {wherein R²¹ and R²² represent each independently a C1-C6 alkyl group optionally having one or more halogen atoms};

Group E: a group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, a halogen atom, an oxo group, a hydroxy group, a cyano group, and a nitro group;

Group F: a group consisting of a C1-C6 alkoxy group optionally having one or more halogen atoms, an amino group, a NHR²¹, a NR²¹R²², a cyano group, a phenyl group optionally having one or more substituents selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and a 3-7 membered nonaromatic heterocyclic group optionally having one or more substituents selected from Group C;

Group G: a group consisting of a halogen atom and a C1-C6 haloalkyl group]

or an N-oxide compound thereof (hereinafter a compound represented by formula (I) or an N-oxide compound thereof is referred to as “compound of the present invention” or “Present compound”).

[2] The compound according to [1], wherein

q represents 0, 1, or 2; and

R³ represents a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group B, a phenyl group optionally having one or more substituents selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, a OR¹², a NR¹¹R¹², a NR^(11a)R^(12a), a NR¹¹C(O)R¹³, a NR²⁹NR¹¹C(O)R¹³, a NR¹¹C(O)OR¹⁴, a C(O)OR¹⁷, a C(O)NR¹¹R¹², a cyano group, a nitro group, or a halogen atom.

[3] The compound according to [1], wherein

q represents 0, 1, or 2;

R³ represents a C1-C6 alkyl group having one or more halogen atoms, a OR¹², or a halogen atom; and

R¹² represents a hydrogen atom or a C1-C3 alkyl group optionally having one or more halogen atoms.

[4] The compound according to any one of [1] to [3], wherein

p represents 0 or 1; and

R⁶ represents a C1-C6 alkyl group optionally having one or more halogen atoms, or a halogen atom.

[5] The compound according to any one of [1] to [3], wherein p represents 0.

[6] The compound according to any one of [1] to [5], wherein R¹ represents a C2-C10 haloalkyl group.

[7] The compound according to any one of [1] to [5], wherein R¹ represents a C3-C5 alkyl group having four or more fluorine atoms.

[8] The compound according to any one of [1] to [7], wherein R² represents a C1-C6 alkyl group optionally having one or more halogen atoms.

[9] The compound according to any one of [1] to [7], wherein R² represents an ethyl group.

[10] The compound according to [1], wherein

R¹ represents a C2-C10 haloalkyl group;

R² represents an ethyl group;

q represents 0 or 1;

R³ represents a C1-C6 alkyl group optionally having one or more halogen atoms, or a halogen atom;

p represents 0 or 1; and

R⁶ represents a C1-C6 alkyl group optionally having one or more halogen atoms, or a halogen atom.

[11] The compound according to [1], wherein

R¹ represents a C3-C5 alkyl group having four or more fluorine atoms;

-   -   R² represents an ethyl group;     -   q represents 0 or 1;     -   R³ represents a C1-C6 alkyl group optionally having one or more         halogen atoms, or a halogen atom; and

p represents 0.

[12] A composition for controlling a harmful arthropod comprising the compound according to any one of [1] to [11] and an inert carrier.

[13] A method for controlling a harmful arthropod which comprises applying an effective amount of the compound according to any one of [1] to [11] to a harmful arthropod or a habitat where a harmful arthropod lives.

Effect of Invention

The Present compound has excellent control efficacies against harmful arthropods, and thus is useful as an active ingredient of an agent for controlling harmful arthropods.

MODE FOR CARRYING OUT THE INVENTION

The substituent(s) in the present invention is/are explained as follows.

When a substituent “optionally having one or more halogen atoms” has two or more halogen atoms, these halogen atoms may be identical to or different from each other.

The expression of “CX—CY” as described herein means that the number of carbon atom is X to Y. For example, the expression of “C1-C6” means that the number of carbon atom is 1 to 6.

The term of “halogen atom” represents fluorine atom, chlorine atom, bromine atom, or iodine atom.

The term of “chain hydrocarbon group” represents an alkyl group, an alkenyl group, and an alkynyl group.

Examples of the term of “alkyl group” include methyl group, ethyl group, propyl group, isopropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, 1-ethylpropyl group, butyl group, tert-butyl group, pentyl group, and hexyl group.

Examples of the term of “alkenyl group” include vinyl group, 1-propenyl group, 2-propenyl group, 1-methyl-1-propenyl group, 1-methyl-2-propenyl group, 1,2-dimethyl-1-propenyl group, 1,1-dimethyl-2-propenyl group, 1-ethyl-1-propenyl group, 1-ethyl-2-propenyl group, 3-butenyl group, 4-pentenyl group, and 5-hexenyl group.

Examples of the term of “alkynyl group” include ethynyl group, 1-propynyl group, 2-propynyl group, 1-methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 1-ethyl-2-propynyl group, 2-butynyl group, 4-pentynyl group, and 5-hexynyl group.

The term of “C2-C10 haloalkyl group” represents a C2-C10 alkyl group wherein one or more hydrogen atoms are substituted with one or more halogen atoms, and examples thereof include a C2-C10 fluoroalkyl group.

Examples of the term of “C2-C10 haloalkyl group” include chloroethyl group, 2,2,2-trifluoroethyl group, 2-bromo-1,1,2,2-tetrafluoroethyl group, 2,2,3,3-tetrafluoropropyl group, 1-methyl-2,2,3,3-tetrafluoropropyl group, perfluorohexyl group, and perfluorodecyl group.

Examples of the term of “C2-C10 fluoroalkyl group” include 2,2,2-trifluoroethyl group, 2,2,3,3-tetrafluoropropyl group, 1-methyl-2,2,3,3-tetrafluoropropyl group, perfluorohexyl group, and perfluorodecyl group.

Examples of the term of “cycloalkyl group” include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, and cycloheptyl group.

The term of “3-7 membered nonaromatic heterocyclic group” represents an aziridine ring, an azetidine ring, a pyrrolidine ring, an imidazoline ring, an imidazolidine ring, a piperidine ring, a tetrahydropyrimidine ring, a hexahydropyrimidine ring, a piperazine ring, an azepane ring, an oxazolidine ring, an isoxazolidine ring, a 1,3-oxazinane ring, a morpholine ring, a 1,4-oxazepane ring, a thiazolidine ring, an isothiazolidine ring, a 1,3-thiazinane ring, a thiomorpholine ring, or a 1,4-thiazepane ring, and examples of “3-7 membered nonaromatic heterocyclic group optionally having one or more substituents selected from Group E” include the following groups.

Examples of the term of “phenyl C1-C3 alkyl group {wherein the phenyl moiety in the phenyl C1-C3 alkyl group may optionally have one or more substituents selected from Group D}” include benzyl group, 2-fluorobenzyl group, 4-chlorobenzyl group, 4-(trifluoromethyl)benzyl group, and 2-[4-(trifluoromethyl)phenyl]ethyl group.

The term of “(C1-C5 alkoxy)C2-C5 alkyl group having one or more halogen atoms” represents a group wherein the (C1-C5 alkoxy) and/or the (C2-C5 alkyl) has one or more halogen atoms, and examples thereof include 2-(trifluoromethoxy)ethyl group, 2,2-difluoro-3-methoxypropyl group, 2,2-difluoro-3-(2,2,2-trifluoroethoxy)propyl group, and 3-(2-chloroethoxy)propyl group.

The term of “(C1-C5 alkylsulfanyl)C2-C5 alkyl group having one or more halogen atoms” represents a group wherein the (C1-C5 alkylsulfanyl) and/or the (C2-C5 alkyl) has one or more halogen atoms, and examples thereof include 2,2-difluoro-2-(trifluoromethylthio)ethyl group.

The term of “(C1-C5 alkylsulfinyl)C2-C5 alkyl group having one or more halogen atoms” represents a group wherein the (C1-C5 alkylsulfinyl) and/or the (C2-C5 alkyl) has one or more halogen atoms, and examples thereof include 2,2-difluoro-2-(trifluoromethanesulfinyl)ethyl group.

The term of “(C1-C5 alkylsulfonyl)C2-C5 alkyl group having one or more halogen atoms” represents a group wherein the (C1-C5 alkylsulfonyl) and/or the (C2-C5 alkyl) has one or more halogen atoms, and examples thereof include 2,2-difluoro-2-(trifluoromethanesulfonyl)ethyl group.

The term of “(C3-C6 cycloalkyl)C1-C3 alkyl group optionally having one or more halogen atoms” represents a group wherein the (C3-C6 cycloalkyl) and/or the (C1-C3 alkyl) may optionally have one or more halogen atoms, and examples thereof include (2,2-difluorocyclopropyl)methyl group, 2-cyclopropyl-1,1,2,2-tetrafluoroethyl group, and 2-(2,2-difluorocyclopropyl)-1,1,2,2-tetrafluoroethyl group.

The term of “(C3-C7 cycloalkyl)C1-C3 alkyl group having one or more substituents selected from Group G” represents a group wherein the (C3-C7 cycloalkyl) and/or the (C1-C3 alkyl) has one or more substituents selected from Group G, and examples thereof include (2,2-difluorocyclopropyl)methyl group, [1-(trifluoromethyl)cyclopropyl]methyl group, [2-(trifluoromethyl)cyclopropyl]methyl group, 2-cyclopropyl-1,1,2,2-tetrafluoroethyl group, 2-cyclopropyl-3,3,3,3-trifluoropropyl group, and 1,1,2,2-tetrafluoro-2-[2-(trifluoromethyl)cyclopropyl]ethyl group.

Examples of the term of “C3-C7 cycloalkyl group having one or more substituents selected from Group G” include 2,2-difluorocyclopropyl group, 1-(2,2,2-trifluoroethyl)cyclopropyl group, and 4-(trifluoromethyl)cyclohexyl group.

The term of “5 or 6 membered aromatic heterocyclic group” represents a 5 membered aromatic heterocyclic group or a 6 membered aromatic heterocyclic group, and the term of “5 membered aromatic heterocyclic group” represents pyrrolyl group, furyl group, thienyl group, pyrazolyl group, imidazolyl group, triazolyl group, tetrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, oxadiazolyl group, or thiadiazolyl group, and the term of “6 membered aromatic heterocyclic group” represents pyridyl group, pyridazinyl group, pyrimidinyl group, or pyrazinyl group.

The term of “5 membered aromatic heterocyclic group comprising 1 to 4 nitrogen atoms” represents pyrrolyl group, pyrazolyl group, imidazolyl group, 1,2,4-triazolyl group, 1,2,3-triazolyl group, or tetrazolyl group.

The term of “N-oxide compound” represents a compound represented by the following formula (I-N1).

[wherein the symbols are the same as defined above.]

Embodiments of the Present compound include the following compounds.

The Present compound, wherein R¹ represents a C2-C10 haloalkyl group or a (C3-C7 cycloalkyl)C1-C3 alkyl group having one or more substituents selected from Group G;

The Present compound, wherein R¹ represents a C2-C10 haloalkyl group;

The Present compound, wherein R¹ represents a C2-C10 alkyl group having two or more fluorine atoms;

The Present compound, wherein R¹ represents a C2-C6 alkyl group having four or more fluorine atoms;

The Present compound, wherein R² represents a C1-C6 alkyl group optionally having one or more halogen atoms;

The Present compound, wherein R² represents a C1-C6 alkyl group;

The Present compound, wherein R² represents a C2-C6 alkyl group;

The Present compound, wherein R² represents a methyl group or an ethyl group;

The Present compound, wherein R² represents an ethyl group;

The Present compound, wherein q represents 0, 1, 2, or 3, and R³ represents a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group B, a phenyl group optionally having one or more substituents selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, a OR¹², a NR¹¹R¹², a NR^(11a)R^(12a), a S(O)_(y)R¹⁵, or a halogen atom;

The Present compound, wherein q represents 0, 1, or 2, and R³ represents each independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a phenyl group optionally having one or more substituents selected from Group D, a 6 membered aromatic heterocyclic group comprising 1 to 2 nitrogen atoms (wherein said 6 membered aromatic heterocyclic group may optionally have one or more substituents selected from Group D), a 5 membered aromatic heterocyclic group comprising 1 to 4 nitrogen atoms (wherein said 5 membered aromatic heterocyclic group may optionally have one or more substituents selected from Group D), a OR¹², a NR¹¹R¹², a NR²⁹NR¹¹R¹², a S(O)_(y)R¹⁵, or a halogen atom;

The Present compound, wherein q represents 0, 1, or 2, and R³ represents each independently a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group B, a phenyl group optionally having one or more substituents selected from Group D, a 6 membered aromatic heterocyclic group selected from Group R (wherein said 6 membered aromatic heterocyclic group may optionally have one or more substituents selected from Group D), a 5 membered aromatic heterocyclic group selected from Group Q (wherein said 5 membered aromatic heterocyclic group may optionally have one or more substituents selected from Group D), a OR¹², a NR¹¹R¹², a NR^(11a)R^(12a), a NR²⁹NR¹¹R¹², a S(O)_(y)R¹⁵, or a halogen atom;

The Present compound, wherein q represents 0, 1, or 2, and R³ represents each independently a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group B, a 6 membered aromatic heterocyclic group selected from Group R (wherein said 6 membered aromatic heterocyclic group may optionally have one or more substituents selected from Group D), a 5 membered aromatic heterocyclic group selected from Group Q (wherein said 5 membered aromatic heterocyclic group may optionally have one or more substituents selected from Group D), a OR¹², a NR¹¹R¹², a NR^(11a)R^(12a), a NR²⁹NR¹¹R¹², a S(O)_(y)R¹⁵, or a halogen atom;

Group R:

The Present compound, wherein q represents 0, 1, or 2, and R³ represents a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group B, a 5 membered aromatic heterocyclic group selected from Group Q (wherein said 5 membered aromatic heterocyclic group may optionally have one or more substituents selected from Group D), a OR¹², a NR¹¹R¹², a NR^(11a)R^(12a), a NR²⁹NR¹¹R¹², a S(O)_(y)R¹⁵, or a halogen atom;

Group Q:

{wherein R²⁶ represents a C1-C6 alkyl group optionally having one or more halogen atoms.}

The Present compound, wherein q represents 0, 1, or 2, and R³ represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a 5 membered aromatic heterocyclic group comprising 1 to 4 nitrogen atoms (wherein said 5 membered aromatic heterocyclic group may optionally have one or more substituents selected from Group D), a OR¹², a NR¹¹R¹², a NR²⁹NR¹¹R¹², a S(O)_(y)R¹⁵, or a halogen atom;

The Present compound, wherein q represents 0 or 1, and R³ represents a C1-C6 alkyl group optionally having one or more halogen atoms, a OR¹², or a halogen atom;

The Present compound, wherein q represents 0 or 1, and R³ represents a C1-C6 alkyl group optionally having one or more halogen atoms, or a halogen atom;

The Present compound, wherein R⁶ represents a C1-C6 alkyl group optionally having one or more halogen atoms, or a halogen atom;

The Present compound, wherein p represents 0 or 1, and R⁶ represents a C1-C6 alkyl group optionally having one or more halogen atoms, or a halogen atom;

The Present compound, wherein p represents 0;

The Present compound, wherein R¹ represents a C2-C10 haloalkyl group,

R² represents a C1-C6 alkyl group optionally having one or more halogen atoms,

q represents 0, 1, 2, or 3, R³ represents a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group B, a 5 membered aromatic heterocyclic group selected from Group Q (wherein said 5 membered aromatic heterocyclic group may optionally have one or more substituents selected from Group D), a OR¹², a NR¹¹R¹², a NR^(11a)R^(12a), a NR²⁹NR¹¹R¹², a S(O)_(y)R¹⁵, or a halogen atom, p represents 0 or 1, and R⁶ represents a C1-C6 alkyl group optionally having one or more halogen atoms, or a halogen atom;

The Present compound, wherein R¹ represents a C2-C10 haloalkyl group,

R² represents an ethyl group,

q represents 0, 1, 2, or 3, R³ represents each independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a phenyl group optionally having one or more substituents selected from Group D, a 6 membered aromatic heterocyclic group comprising 1 to 2 nitrogen atoms (wherein said 6 membered aromatic heterocyclic group may optionally have one or more substituents selected from Group D), a 5 membered aromatic heterocyclic group comprising 1 to 4 nitrogen atoms (wherein said 5 membered aromatic heterocyclic group may optionally have one or more substituents selected from Group D) a OR¹², a NR¹¹R¹², a NR²⁹NR¹¹R¹², a S(O)_(y)R¹⁵, or a halogen atom, R¹¹ and R¹² represent each independently a hydrogen atom or a C1-C3 alkyl group optionally having one or more halogen atoms, R¹⁵ represents a C1-C3 alkyl group optionally having one or more halogen atoms, p represents 0 or 1, and R⁶ represents a C1-C6 alkyl group optionally having one or more halogen atoms, or a halogen atom;

The Present compound, wherein R¹ represents a C2-C10 haloalkyl group,

R² represents an ethyl group,

q represents 0, 1, 2, or 3, R³ represents each independently a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group B, a 6 membered aromatic heterocyclic group selected from Group R (wherein said 6 membered aromatic heterocyclic group may optionally have one or more substituents selected from Group D), a 5 membered aromatic heterocyclic group selected from Group Q (wherein said 5 membered aromatic heterocyclic group may optionally have one or more substituents selected from Group D), a OR¹², a NR¹¹R¹², a NR^(11a)R^(12a), a NR²⁹NR¹¹R¹², a S(O)_(y)R¹⁵, or a halogen atom, R¹¹ and R¹² represent each independently a hydrogen atom or a C1-C3 alkyl group optionally having one or more halogen atoms, R¹⁵ represents a C1-C3 alkyl group optionally having one or more halogen atoms, p represents 0 or 1, and R⁶ represents a C1-C6 alkyl group optionally having one or more halogen atoms, or a halogen atom;

The Present compound, wherein R¹ represents a C2-C10 haloalkyl group,

R² represents an ethyl group,

q represents 0, 1, 2, or 3, R³ represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a 5 membered aromatic heterocyclic group comprising 1 to 4 nitrogen atoms (wherein said 5 membered aromatic heterocyclic group may optionally have one or more substituents selected from Group D), a OR¹², a NR¹¹R¹², a NR²⁹NR¹¹R¹², a S(O)_(y)R¹⁵, or a halogen atom, R¹¹ and R¹² represent each independently a hydrogen atom or a C1-C3 alkyl group optionally having one or more halogen atoms, R¹⁵ represents a C1-C3 alkyl group optionally having one or more halogen atoms, p represents 0 or 1, and R⁶ represents a C1-C6 alkyl group optionally having one or more halogen atoms, or a halogen atom;

The Present compound, wherein R¹ represents a C2-C10 alkyl group having two or more fluorine atoms,

R² represents an ethyl group,

q represents 0, 1, 2, or 3, R³ represents a C1-C6 alkyl group optionally having one or more halogen atoms, a OR¹², or a halogen atom,

R¹² represents a hydrogen atom or a C1-C3 alkyl group optionally having one or more halogen atoms, and

p represents 0;

The Present compound, wherein R¹ represents a C3-C6 alkyl group having four or more fluorine atoms,

R² represents an ethyl group,

q represents 0, 1, 2, or 3, R³ represents a C1-C6 alkyl group optionally having one or more halogen atoms, a 5 membered aromatic heterocyclic group selected from Group Q (wherein said 5 membered aromatic heterocyclic group may optionally have one or more substituents selected from Group D), a OR¹², a NR¹¹R¹², a NR^(11a)R^(12a), a S(O)_(y)R¹⁵, or a halogen atom, R¹¹ and R¹² represent each independently a hydrogen atom or a C1-C3 alkyl group optionally having one or more halogen atoms, R¹⁵ represents a C1-C3 alkyl group optionally having one or more halogen atoms, p represents 0 or 1, and R⁶ represents a C1-C6 alkyl group optionally having one or more halogen atoms, or a halogen atom;

The Present compound, wherein R¹ represents a C3-C6 haloalkyl group having four or more fluorine atoms,

R² represents an ethyl group,

q represents 0, 1, 2, or 3, R³ represents a C1-C6 alkyl group optionally having one or more halogen atoms, a OR¹², or a halogen atom,

R¹² represents a hydrogen atom or a C1-C3 alkyl group optionally having one or more halogen atoms, and

p represents 0;

The compound represented by formula (I), wherein R¹ represents a C2-C10 haloalkyl group, R² represents a C1-C6 alkyl group, q represents 0 or 1, R³ represents a C1-C6 alkyl group optionally having one or more halogen atoms, a OR¹², or a halogen atom, R¹² represents a C1-C6 alkyl group optionally having one or more halogen atoms, and p represents 0.

The compound represented by formula (I), wherein R¹ represents a C2-C10 alkyl group having one or more halogen atoms, a C3-C10 alkenyl group having one or more halogen atoms, a (C1-C5 alkoxy)C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfanyl)C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfinyl)C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfonyl)C2-C5 alkyl group having one or more halogen atoms, or a (C3-C7 cycloalkyl)C1-C3 alkyl group having one or more halogen atoms, R² represents a C1-C6 alkyl group, q represents 0 or 1, R³ represents a C1-C6 alkyl group optionally having one or more halogen atoms, a OR¹², a S(O)_(y)R¹⁵, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, or a halogen atom, R¹² and R¹⁵ represent each independently a C1-C6 alkyl group optionally having one or more halogen atoms, and p represents 0.

Next, a process for preparing the Present compound is described.

The Present compound may be prepared, for example, according to the following processes.

Process 1

A compound represented by formula (Ib) (hereinafter referred to as “Present compound (Ib)”) and a compound represented by formula (Ic) (hereinafter referred to as “Present compound (Ic)”) may be prepared by reacting a compound represented by formula (Ia) (hereinafter referred to as “Present compound (Ia)”) with an oxidizing agent.

[wherein the symbols are the same as defined above.]

First, a process for preparing the Present compound (Ib) from the Present compound (Ia) is described.

The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform (hereinafter collectively referred to as “aliphatic halogenated hydrocarbons”); nitriles such as acetonitrile (hereinafter collectively referred to as “nitriles”); esters such as ethyl acetate; alcohols such as methanol and ethanol (hereinafter collectively referred to as “alcohols”); acetic acid; water; and mixed solvents thereof.

Examples of the oxidizing agent to be used in the reaction include sodium periodate, m-chloroperbenzoic acid (hereinafter referred to as “mCPBA”), and hydrogen peroxide.

When hydrogen peroxide is used as the oxidizing agent, sodium carbonate or a catalyst may be added to the reaction as needed.

Examples of the catalyst to be used in the reaction include tungstic acid and sodium tungstate.

In the reaction, the oxidizing agent is usually used within a range of 1 to 1.2 molar ratio(s), the base is usually used within a range of 0.01 to 1 molar ratio(s), and the catalyst is usually used within a range of 0.01 to 0.5 molar ratios, relative to 1 mole of the Present compound (Ia).

The reaction temperature of the reaction is usually within a range of −20 to 80° C. The reaction period of the reaction is usually within a range of 0.1 to 12 hours.

When the reaction is completed, the reaction mixture is extracted with organic solvent(s), and the organic layers are sequentially washed with an aqueous solution of a reducing agent (for example, sodium sulfite or sodium thiosulfate) and an aqueous solution of a base (for example, sodium hydrogen carbonate) as needed. The resulting organic layers are dried and concentrated to give the Present compound (Ib).

Next, a process for preparing the Present compound (Ic) from the Present compound (Ib) is described.

The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include aliphatic halogenated hydrocarbons, nitriles, alcohols, acetic acid, water, and mixed solvents thereof.

Examples of the oxidizing agent to be used in the reaction include mCPBA and hydrogen peroxide.

When hydrogen peroxide is used as the oxidizing agent, a base or a catalyst may be added to the reaction as needed.

Examples of the base to be used in the reaction include sodium carbonate.

Examples of the catalyst to be used in the reaction include sodium tungstate.

In the reaction, the oxidizing agent is usually used within a range of 1 to 2 molar ratio(s), the base is usually used within a range of 0.01 to 1 molar ratio(s), and the catalyst is usually used within a range of 0.01 to 0.5 molar ratios, relative to 1 mole of the Present compound (Ib).

The reaction temperature of the reaction is usually within a range of −20 to 120° C. The reaction period of the reaction is usually within a range of 0.1 to 12 hours.

When the reaction is completed, the reaction mixture is extracted with organic solvent(s), and the organic layers are sequentially washed with an aqueous solution of a reducing agent (for example, sodium sulfite or sodium thiosulfate) and an aqueous solution of a base (for example, sodium hydrogen carbonate) as needed. The organic layers are dried and concentrated to give the Present compound (Ic).

Also, the Present compound (Ic) may be prepared in one step reaction (one-pot) by reacting the Present compound (Ia) with an oxidizing agent.

The reaction may be carried out by using the oxidizing agent usually at 2.0 to 2.4 molar ratios relative to 1 mole of the Present compound (Ia) according to the process for preparing the Present compound (Ic) from the Present compound (Ib)

Process 2

The Present compound represented by formula (I) (hereinafter referred to as “Present compound (I)”) may be prepared by reacting a compound represented by formula (M-3) (hereinafter referred to as “Compound (M-3)”) with a compound represented by formula (R-3) (hereinafter referred to as “Compound (R-3)”) in the presence of a base.

[wherein: V¹ represents a halogen atom, a C1-C10 perfluoroalkanesulfonyloxy group, or a tosyloxy group; and the other symbols are the same as defined above.]

The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, methyl-tert-butyl ether (hereinafter referred to as “MTBE”), and 1,4-dioxane (hereinafter collectively referred to as “ethers”); aliphatic halogenated hydrocarbons; aromatic hydrocarbons such as toluene and xylene (hereinafter collectively referred to as “aromatic hydrocarbons”); aprotic polar solvents such as dimethylformamide (hereinafter referred to as “DMF”), N-methylpyrrolidone (hereinafter referred to as “NMP”), and dimethyl sulfoxide (hereinafter referred to as “DMSO”) (hereinafter collectively referred to as “aprotic polar solvents”); and mixed solvents thereof.

Examples of the base to be used in the reaction include organic bases such as triethylamine, diisopropylethylamine, pyridine, and 4-(dimethylamino)pyridine (hereinafter collectively referred to as “organic bases”); alkali metal hydrides such as sodium hydride (hereinafter collectively referred to as “alkali metal hydrides”); and alkali metal carbonates such as sodium carbonate and potassium carbonate (hereinafter collectively referred to as “alkali metal carbonates”).

In the reaction, the Compound (R-3) is usually used within a range of 1 to 10 molar ratio(s), and the base is usually used within a range of 0.1 to 5 molar ratios, relative to 1 mole of the Compound (M-3).

The reaction temperature of the reaction is usually within a range of −20° C. to 120° C. The reaction period of the reaction is usually within a range of 0.1 to 24 hours.

When the reaction is completed, the reaction mixture is extracted with organic solvent(s), and the organic layers are worked up (for example, dried or concentrated) to give the Present compound (I).

Process 3

The Present compound (Ia) may be prepared by reacting a compound represented by formula (M-1) (hereinafter referred to as “Compound (M-1)”) with a compound represented by formula (R-1) (hereinafter referred to as “Compound (R-1)”) in the presence of a base.

[wherein: V represents a halogen atom; and the other symbols are the same as defined above.]

The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixed solvents thereof.

Examples of the base to be used in the reaction include alkali metal carbonates and alkali metal hydrides.

In the reaction, the Compound (R-1) is usually used within a range of 1 to 10 molar ratio(s), and the base is usually used within a range of 1 to 10 molar ratio(s), relative to 1 mole of the Compound (M-1).

The reaction temperature of the reaction is usually within a range of −20° C. to 150° C. The reaction period of the reaction is usually within a range of 0.5 to 24 hours.

When the reaction is completed, the reaction mixture is extracted with organic solvent(s), and the organic layers are worked up (for example, dried or concentrated) to give the Present compound (Ia).

V is preferably a fluorine atom.

Process 4

The Present compound (I) may be prepared by reacting a compound represented by formula (M-4) (hereinafter referred to as “Compound (M-4)”) with a compound represented by formula (R-15) (hereinafter referred to as “Compound (R-15)”) in the presence of a base.

[wherein the symbols are the same as defined above.]

The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixed solvents thereof.

Examples of the base to be used in the reaction include alkali metal carbonates and alkali metal hydrides.

In the reaction, the Compound (R-4) is usually used within a range of 1 to 10 molar ratio(s), and the base is usually used within a range of 1 to 10 molar ratio(s), relative to 1 mole of the Compound (M-4).

The reaction temperature of the reaction is usually within a range of −20° C. to 150° C. The reaction period of the reaction is usually within a range of 0.5 to 24 hours.

When the reaction is completed, the reaction mixture is extracted with organic solvent(s), and the organic layers are worked up (for example, dried or concentrated) to give the Present compound (I).

V is preferably a fluorine atom.

Hereinafter, a process for preparing each Intermediate compound is described.

Reference Process 1

The Compound (M-1) may be prepared by reacting a compound represented by formula (M-8) (hereinafter referred to as “Compound (M-8)”) with a compound represented by formula (M-9) (hereinafter referred to as “Compound (M-9)”) in the presence of a metal catalyst.

[wherein: V³ represents a chlorine atom, a bromine atom, or an iodine atom; M represents a B(OR⁴⁰)₂, a 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group, a Sn(n-C₄H₉)₃, a ZnCl, a MgCl, or a MgBr; R⁴⁰ represents a hydrogen atom or a C1-C6 alkyl group; and the other symbols are the same as defined above.]

The Compound (M-9) may be prepared according to, for example, the process described in WO 03/024961 pamphlet or the process described in Organic Process Research & Development, 2004, 8, 192-200.

The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include ethers, aromatic hydrocarbons, aprotic polar solvents, water, and mixed solvents thereof.

Examples of the metal catalyst to be used in the reaction include palladium catalysts such as tetrakis(triphenylphosphine)palladium(0), 1,1′-bis(diphenylphosphino)ferrocene palladium(II) dichloride, tris(dibenzylideneacetone)dipalladium(0), and palladium(II) acetate; nickel catalysts such as bis(cyclooctadiene)nickel(0) and nickel(II) chloride; and copper catalysts such as copper(I) iodide and copper(I) chloride.

A ligand, a base, and/or an inorganic halide may be added to the reaction as needed.

Examples of the ligand to be used in the reaction include triphenylphosphine, Xantphos, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, 1,1′-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl, 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2′-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, and 1,10-phenanthroline.

Examples of the base to be used in the reaction include alkali metal hydrides, alkali metal carbonates, and organic bases.

Examples of the inorganic halide to be used in the reaction include alkali metal fluorides such as potassium fluoride and sodium fluoride; and alkali metal chlorides such as lithium chloride and sodium chloride.

In the reaction, the Compound (M-9) is usually used within a range of 1 to 10 molar ratio(s), the metal catalyst is usually used within a range of 0.01 to 0.5 molar ratios, the ligand is usually used within a range of 0.01 to 1 molar ratio(s), the base is usually used within a range of 0.1 to 5 molar ratios, and the inorganic halide is usually used within a range of 0.1 to 5 molar ratios, relative to 1 mole of the Compound (M-8).

The reaction temperature of the reaction is usually within a range of −20° C. to 200° C. The reaction period of the reaction is usually within a range of 0.1 to 24 hours.

When the reaction is completed, the reaction mixture is extracted with organic solvent(s), and the organic layers are worked up (for example, dried or concentrated) to give the Compound (M-1).

Reference Process 2

The Compound (M-3) may be prepared by reacting a compound represented by formula (M-11) (hereinafter referred to as “Compound (M-11)”) with an acid.

[wherein: R^(x) represents a methyl group or an ethyl group; and the other symbols are the same as defined above.]

The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include aliphatic halogenated hydrocarbons, aromatic hydrocarbons, nitriles, alcohols, acetic acid, water, and mixed solvents thereof.

Examples of the acid to be used in the reaction include mineral acids such as hydrochloric acid; halogenated borons such as boron trichloride and boron tribromide; and metal chlorides such as titanium chloride and aluminum chloride.

In the reaction, the acid is usually used within a range of 0.1 to 10 molar ratio(s) relative to 1 mole of the Compound (M-11). When a mineral acid is used as the acid, the mineral acid may be used also as a solvent.

The reaction temperature of the reaction is usually within a range of −20° C. to 150° C. The reaction period of the reaction is usually within a range of 0.1 to 24 hours.

When the reaction is completed, the reaction mixture is extracted with organic solvent(s), and the organic layers are worked up (for example, dried or concentrated) to give the Compound (M-3).

Reference Process 3

In the Compound (M-11), a compound wherein n represents 0 (hereinafter referred to as “Compound (M-11a)”), a compound wherein n represents 1 (hereinafter referred to as “Compound (M-11b)”), and a compound wherein n represents 2 (hereinafter referred to as “Compound (M-11c)”) may be prepared according to the following process.

[wherein the symbols are the same as defined above.]

The Compound (M-13) may be prepared by using a compound represented by formula (M-12) (hereinafter referred to as “Compound (M-12)”) instead of the Compound (M-8) according to the process described in the Reference process 1.

The Compound (M-12) is a commercially available compound or may be prepared according to a known process.

The Compound (M-11a) may be prepared by using the Compound (M-13) instead of the Compound (M-1) according to the process described in the Process 3.

The Compound (M-11b) and the Compound (M-11c) may be prepared by using the Compound (M-1a) instead of the Present compound (Ia) according to the process described in the Process 1.

Reference Process 4

A compound represented by formula (M-4a) (hereinafter referred to as “Compound (M-4a)”) and a compound represented by formula (M-4b) (hereinafter referred to as “Compound (M-4b)”) may be prepared according to the following process.

[wherein: V⁴ represents a chlorine atom or a bromine atom; V⁵ represents a fluorine atom or an iodine atom; and the other symbols are the same as defined above.]

First, a process for preparing the Compound (M-4a) from the Compound (M-3) is described.

The Compound (M-4a) may be prepared by reacting the Compound (M-3) with phosphorus oxychloride or phosphorus oxybromide.

The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include aromatic hydrocarbons.

When phosphorus oxychloride is used, phosphorus oxychloride may be used also as a solvent.

In the reaction, phosphorus oxychloride or phosphorus oxybromide is usually used within a range of 1 to 10 molar ratio(s) relative to 1 mole of the Compound (M-3).

The reaction temperature of the reaction is usually within a range of 0° C. to 150° C. The reaction period of the reaction is usually within a range of 0.5 to 24 hours.

When the reaction is completed, the reaction mixture is extracted with organic solvent(s), and the organic layers are worked up (for example, dried or concentrated) to give the Compound (M-4a).

Next, a process for preparing the Compound (M-4b) from the Compound (M-4a) is described.

The Compound (M-4b) may be prepared by reacting the Compound (M-4a) with an inorganic fluoride or an inorganic iodide.

The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include nitriles, aprotic polar solvents, nitrogen-containing aromatic compounds, and mixed solvents thereof.

Examples of the inorganic fluoride to be used in the reaction include potassium fluoride, sodium fluoride, and cesium fluoride.

Examples of the inorganic iodide to be used in the reaction include potassium iodide and sodium iodide.

When the Compound (M-4b) wherein V⁵ represents a fluorine atom is prepared, the inorganic fluoride is usually used within a range of 1 to 10 molar ratio(s) relative to 1 mole of the Compound (M-4a).

When the Compound (M-4b) wherein V⁵ represents an iodine atom is prepared, the inorganic iodide is usually used within a range of 1 to 10 molar ratio(s) relative to 1 mole of the Compound (M-4a).

The reaction temperature of the reaction is usually within a range of 0° C. to 250° C. The reaction period of the reaction is usually within a range of 0.5 to 24 hours.

When the reaction is completed, the reaction mixture is extracted with organic solvent(s), and the organic layers are worked up (for example, dried or concentrated) to give the Compound (M-4b).

Next, specific examples of the Present compound are shown below.

The Present compound represented by formula (1-A)

wherein n represents 2, R^(3b) represents a trifluoromethyl group, R^(3a), R^(3c), R^(3d), R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R² represent any one combination indicated in Table 1 to Table 5 (hereinafter referred to as “Compound group SX1”).

TABLE 1 R¹ R² CF₂HCH₂ CH₃CH₂ CH₃CF₂ CH₃CH₂ CF₃CH₂ CH₃CH₂ CCl₃CH₂ CH₃CH₂ CF₂HCF₂ CH₃CH₂ CHClFCF₂ CH₃CH₂ CF₃CH₂CH₂ CH₃CH₂ CF₂HCF₂CH₂ CH₃CH₂ CF₃CF₂CH₂ CH₃CH₂ CBrF₂CF₂ CH₃CH₂ CF₃CFHCF₂ CH₃CH₂ CH₃CF₂CH₂ CH₃CH₂ CF₃CH(CH₃) CH₃CH₂ CF₃C(CH₃)₂ CH₃CH₂ CH(CH₃)₂CH(CF₃) CH₃CH₂ (CF₃)₂CH CH₃CH₂ CH₃CH₂CH(CF₃) CH₃CH₂ CF₃CCl₂CH₂ CH₃CH₂ CF₃CF₂CH(CH₃) CH₃CH₂ CF₃CF₂CH(CH₂CH₃) CH₃CH₂ C(CH₃)(CF₃)₂CH₂ CH₃CH₂ CF₃CFHCF₂CH₂ CH₃CH₂ CF₃(CF₂)₂CH₂ CH₃CH₂ CBrF₂CF₂CH₂CH₂ CH₃CH₂ CF₃CFHCF₂CH(CH₃) CH₃CH₂

TABLE 2 R¹ R² CF₃CH═CHCH₂ CH₃CH₂ CF₃(CF₂)₃CH₂ CH₃CH₂ CF₃(CF₂)₄CH₂ CH₃CH₂ CF₃(CF₂)₃CH₂CH₂ CH₃CH₂ CF(CF₃)₂CF₂CF₂CH₂CH₂ CH₃CH₂ CF₂H(CF₂)₃CH₂ CH₃CH₂ CF₂H(CF₂)₅CH₂ CH₃CH₂ CF₃(CF₂)₃CH₂CH₂CH₂ CH₃CH₂ CF₃CF₂(CH₂)₅CH₂ CH₃CH₂ CF₃(CF₂)₅CH₂CH₂CH₂ CH₃CH₂ CF₃(CF₂)₃CH₂(CH₂)₄CH₂ CH₃CH₂ CF₃(CF₂)₅CH₂CH₂ CH₃CH₂ CF(CF₃)₂CH₂(CH₂)₄CH₂ CH₃CH₂ CF₃OCFHCF₂ CH₃CH₂ CH₃OCH₂CF₂CH₂ CH₃CH₂ CF₃CH₂OCH₂CF₂CH₂ CH₃CH₂ CH₂FCF₂CH₂ CH₃CH₂ CH₂ClCF₂CH₂ CH₃CH₂ CH₂BrCF₂CH₂ CH₃CH₂ CH₃OCH₂(CF₂)₂CH₂ CH₃CH₂ CF₃CH₂OCH₂(CF₂)₂CH₂ CH₃CH₂ CH₂F(CF₂)₂CH₂ CH₃CH₂ CH₂Cl(CF₂)₂CH₂ CH₃CH₂ CH₂Br(CF₂)₂CH₂ CH₃CH₂ CH₃OCH₂(CF₂)₃CH₂ CH₃CH₂

TABLE 3 R¹ R² CF₃CH₂OCH₂(CF₂)₃CH₂ CH₃CH₂ CH₃OCH₂(CF₂)₃CH₂ CH₃CH₂ CF₃CH₂OCH₂(CF₂)₃CH₂ CH₃CH₂ CH₂F(CF₂)₃CH₂ CH₃CH₂ CH₂Cl(CF₂)₃CH₂ CH₃CH₂ CH₂Br(CF₂)₃CH₂ CH₃CH₂ CH₃OCH₂(CF₂)₄CH₂ CH₃CH₂ CF₃CH₂OCH₂(CF₂)₄CH₂ CH₃CH₂ CH₂F(CF₂)₄CH₂ CH₃CH₂ CH₂Cl(CF₂)₄CH₂ CH₃CH₂ CH₂Br(CF₂)₄CH₂ CH₃CH₂ CF₃CF₂OCFHCF₂ CH₃CH₂ CF₃CF₂CF₂OCFHCF₂ CH₃CH₂ CF₃CF₂CF₂OCF(CF₃)CH₂ CH₃CH₂ CF₃CH₂OCH₂CH₂ CH₃CH₂

TABLE 4 R¹ R²

CH₃CH₂

CH₃CH₂

CH₃CH₂

CH₃CH₂

CH₃CH₂

CH₃CH₂

CH₃CH₂

TABLE 5 R¹ R² CH₃SCH₂CF₂CH₂ CH₃CH₂ CH₃S(O)CH₂CF₂CH₂ CH₃CH₂ CH₃S(O)₂CH₂CF₂CH₂ CH₃CH₂ CF₃CH₂SCH₂CF₂CH₂ CH₃CH₂ CF₃CH₂S(O)CH₂CF₂CH₂ CH₃CH₂ CF₃CH₂S(O)₂CH₂CF₂CH₂ CH₃CH₂ CF₃SCH₂CF₂CH₂ CH₃CH₂ CF₃S(O)CH₂CF₂CH₂ CH₃CH₂ CF₃S(O)₂CH₂CF₂CH₂ CH₃CH₂ CF₃SCH₂(CF₂)₂CH₂ CH₃CH₂ CF₃S(O)CH₂(CF₂)₂CH₂ CH₃CH₂ CF₃S(O)₂CH₂(CF₂)₂CH₂ CH₃CH₂ CF₃SCH₂(CF₂)₃CH₂ CH₃CH₂ CF₃S(O)CH₂(CF₂)₃CH₂ CH₃CH₂ CF₃S(O)₂CH₂(CF₂)₃CH₂ CH₃CH₂ CF₃SCH₂(CF₂)₄CH₂ CH₃CH₂ CF₃S(O)CH₂(CF₂)₄CH₂ CH₃CH₂ CF₃S(O)₂CH₂(CF₂)₄CH₂ CH₃CH₂ CF₃CH₂SCH₂CH₂ CH₃CH₂ CF₃CH₂S(O)CH₂CH₂ CH₃CH₂ CF₃CH₂S(O)₂CH₂CH₂ CH₃CH₂ CF₃SCH₂CH₂ CH₃CH₂ CF₃S(O)CH₂CH₂ CH₃CH₂ CF₃S(O)₂CH₂CH₂ CH₃CH₂

The Present compound represented by formula (I-A), wherein n represents 2, R^(3a), R^(3b), R^(3c), R^(3d), R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R² represent any one combination indicated in Table 1 to Table 5 (hereinafter referred to as “Compound group SX2”).

The Present compound represented by formula (I-A), wherein n represents 2, R^(3b) represents a chlorine atom, R^(3a)R^(3c), R^(3d), R^(6a), R^(6b) and R^(6c) represent each a hydrogen atom, and R¹ and R² represent any one combination indicated in Table 1 to Table 5 (hereinafter referred to as “Compound group SX3”).

The Present compound represented by formula (I-A), wherein n represents 2, R^(3b) represents a fluorine atom, R^(3a), R^(3c), R^(3d), R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹⁰¹ and R¹⁰² represent any one combination indicated in Table 1 to Table 5 (hereinafter referred to as “Compound group SX4”).

The Present compound represented by formula (I-A), wherein n represents 2, R^(3b) represents a bromine atom, R^(3a), R^(3c), R^(3d), R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹⁰¹ and R¹⁰² represent any one combination indicated in Table 1 to Table 5 (hereinafter referred to as “Compound group SX5”).

The Present compound represented by formula (I-A), wherein n represents 2, R^(3b) represents a trifluoromethoxy group, R^(3a), R^(3c), R^(3d), R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R² represent any one combination indicated in Table 1 to Table 5 (hereinafter referred to as “Compound group SX6”).

The Present compound represented by formula (I-A), wherein n represents 2, R^(3b) represents a trifluoromethylthio group, R^(3a), R^(3c), R^(3d), R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R² represent any one combination indicated in Table 1 to Table 5 (hereinafter referred to as “Compound group SX7”).

The Present compound represented by formula (I-A), wherein n represents 2, R^(3b) represents a trifluoromethylsulfinyl group, R^(3a), R^(3c), R^(3d), R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R² represent any one combination indicated in Table 1 to Table 5 (hereinafter referred to as “Compound group SX8”).

The Present compound represented by formula (I-A), wherein n represents 2, R^(3b) represents a trifluoromethylsulfonyl group, R^(3a), R^(3c)R^(3d), R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R² represent any one combination indicated in Table 1 to Table 5 (hereinafter referred to as “Compound group SX9”).

The Present compound represented by formula (I-A), wherein n represents 2, R^(3b) represents a pentafluoroethyl group, R^(3a), R^(3c), R^(3d), R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R and R² represent any one combination indicated in Table 1 to Table 5 (hereinafter referred to as “Compound group SX10”).

The Present compound represented by formula (I-A), wherein n represents 2, R^(3b) represents a pentafluorosulfanyl group, R^(3a), R^(3c)R^(3d), R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R² represent any one combination indicated in Table 1 to Table 5 (hereinafter referred to as “Compound group SX11”).

The Present compound represented by formula (I-A), wherein n represents 2, R^(3b) represents a pyridin-2-yl group, R^(3a), R^(3c), R^(3d), R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R² represent any one combination indicated in Table 1 to Table 5 (hereinafter referred to as “Compound group SX12”).

The Present compound represented by formula (I-A), wherein n represents 2, R^(3b) represents a pyridin-3-yl group, R^(3a), R^(3c), R^(3d), R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R² represent any one combination indicated in Table 1 to Table 5 (hereinafter referred to as “Compound group SX13”).

The Present compound represented by formula (I-A), wherein n represents 2, R^(3b) represents a pyridin-4-yl group, R^(3a), R^(3c), R^(3d), R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R² represent any one combination indicated in Table 1 to Table 5 (hereinafter referred to as “Compound group SX14”).

The Present compound represented by formula (I-A), wherein n represents 2, R^(3b) represents a pyridazin-3-yl group, R^(3a), R^(3c), R^(3d), R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R² represent any one combination indicated in Table 1 to Table 5 (hereinafter referred to as “Compound group SX15”).

The Present compound represented by formula (I-A), wherein n represents 2, R^(3b) represents a pyridazin-4-yl group, R^(3a), R^(3c), R^(3d), R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R² represent any one combination indicated in Table 1 to Table 5 (hereinafter referred to as “Compound group SX16”).

The Present compound represented by formula (I-A), wherein n represents 2, R^(3b) represents a pyrimidin-2-yl group, R^(3a), R^(3c), R^(3d), R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R² represent any one combination indicated in Table 1 to Table 5 (hereinafter referred to as “Compound group SX17”).

The Present compound represented by formula (I-A), wherein n represents 2, R^(3b) represents a pyrimidin-4-yl group, R^(3a), R^(3c)R^(3d), R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R² represent any one combination indicated in Table 1 to Table 5 (hereinafter referred to as “Compound group SX18”).

The Present compound represented by formula (I-A), wherein n represents 2, R^(3b) represents a pyrimidin-5-yl group, R^(3a), R^(3c), R^(3d), R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R² represent any one combination indicated in Table 1 to Table 5 (hereinafter referred to as “Compound group SX19”).

The Present compound represented by formula (I-A), wherein n represents 2, R^(3b) represents a pyrazin-5-yl group, R^(3a), R^(3c), R^(3d), R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R² represent any one combination indicated in Table 1 to Table 5 (hereinafter referred to as “Compound group SX20”).

The Present compound may be mixed with or used in combination with a known pesticide, miticide, nematicide, fungicide, plant growth regulator, or synergist such as the followings. Hereinafter, examples of combinations of active ingredients which may be mixed with or used in combination with are described. The abbreviation of “SX” indicates “any one of the Present compound selected from the Compound groups SX1 to SX20”. Also, the number in parentheses represents the CAS registration number.

clothianidin (205510-53-8)+SX, thiamethoxam (153719-23-4)+SX, imidacloprid (138261-41-3)+SX, thiacloprid (111988-49-9)+SX, flupyradifurone (951659-40-8)+SX, sulfoxaflor (946578-00-3)+SX, triflumezopyrim (1263133-33-0)+SX, dicloromezotiaz (1263629-39-5)+SX, beta-cyfluthrin (68359-37-5)+SX, tefluthrin (79538-32-2)+SX, fipronil (120068-37-3)+SX, chlorantraniliprole (500008-45-7)+SX, cyantraniliprole (736994-63-1)+SX, tetraniliprole (1229654-66-3)+SX, thiodicarb (59669-26-0)+SX, carbofuran (1563-66-2)+SX, fluxametamide (928783-29-3)+SX, afoxolaner (1093861-60-9)+SX, fluralaner (864731-61-3)+SX, broflanilide (1207727-04-5)+SX, tebuconazole (107534-96-3)+SX, prothioconazole (178928-70-6)+SX, metconazole (125116-23-6)+SX, ipconazole (125225-28-7)+SX, triticonazole (131983-72-7)+SX, difenoconazole (119446-68-3)+SX, imazalil (35554-44-0)+SX, triadimenol (55219-65-3)+SX, tetraconazole (112281-77-3)+SX, flutriafol (76674-21-0)+SX, mandestrobin (173662-97-0)+SX, azoxystrobin (131860-33-8)+SX, pyraclostrobin (175013-18-0)+SX, trifloxystrobin (141517-21-7)+SX, fluoxastrobin (193740-76-0)+SX, picoxystrobin (117428-22-5)+SX, fenamidone (161326-34-7)+SX, metalaxyl (57837-19-1)+SX, metalaxyl-M (70630-17-0)+SX, fludioxonil (131341-86-1)+SX, sedaxane (874967-67-6)+SX, penflufen (494793-67-8)+SX, fluxapyroxad (907204-31-3)+SX, fluopyram (658066-35-4)+SX, benzovindiflupyr (1072957-71-1)+SX, boscalid (188425-85-6)+SX, carboxin (5234-68-4)+SX, penthiopyrad (183675-82-3)+SX, flutolanil (66332-96-5)+SX, captan (133-06-2)+SX, thiram (137-26-8)+SX, tolclofos-methyl (57018-04-9)+SX, thiabendazole (148-79-8)+SX, ethaboxam (162650-77-3)+SX, mancozeb (8018-01-7)+SX, picarbutrazox (500207-04-5)+SX, oxathiapiprolin (1003318-67-9)+SX, silthiofam (175217-20-6)+SX, abamectin (71751-41-2)+SX, fluensulfone (318290-98-1)+SX, fluazaindolizine (1254304-22-7)+SX, tioxazafen (330459-31-9)+SX, 3-difluoromethyl-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide (141573-94-6)+SX, 3-difluoromethyl-1-methyl-N-[(3R)-1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide (1352994-67-2)+SX, the compound represented by the following formula:

(1689566-03-7)+SX, Mycorrhiza Fungi+SX, Bacillus firmus+SX, Bacillus amyloliquefaciens+SX, Pasteuria nishizawae+SX, and Pasteuria penetrans+SX.

Examples of the harmful arthropod on which the Present compound has efficacies include harmful insects and harmful mites. Specific examples of the harmful arthropod include the followings.

Hemiptera Pests:

Delphacidae (for example, Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, or Peregrinus maidis);

Cicadellidae (for example, Nephotettix cincticeps, Nephotettix virescens, Nephotettix nigropictus (Rice green leafhopper), Recilia dorsalis, Empoasca onukii, Empoasca fabae, Dalbulus maidis, Mahanarva posticata (Sugarcane froghopper), Mahanarva fimbriolota (Sugarcane root spittlebug), Cofana spectra, Nephotettix nigropictus, or Recilia dorsalis);

Aphididae (for example, Aphis gossypii, Myzus persicae, Brevicoryne brassicae, Aphis spiraecola, Macrosiphum euphorbiae, Aulacorthum solani, Rhopalosiphum padi, Toxoptera citricidus, Hyalopterus pruni, Aphis glycines Matsumura, Rhopalosiphum maidis, Tetraneura nigriabdominalis, Viteus vitifoliae, Daktulosphaira vitifoliae (Grape Phylloxera), Phylloxera devastatrix Pergande (Pecan phylloxera), Phylloxera notabilis pergande (Pecan leaf phylloxera), or Phylloxera russellae Stoetzel (Southern pecan leaf phylloxera));

Pentatomidae (for example, Scotinophara lurida, Scotinophara coarctata (Malayan rice black bug), Nezara antennata, Eysarcoris parvus, Halyomorpha mista, Nezara viridula, Euschistus heros (Brown stink bug), Nezara viridula (Southern green stink bug), Piezodorus guildinii (Red banded stink bug), Scaptocoris castanea (Burrower brown bug), Oebalus pugnax, or Dichelops melacanthus);

Alydidae (for example, Riptortus clavetus, Leptocorisa chinensis, Leptocorisa acuta, or Leptocorisa spp.);

Miridae (for example, Trigonotylus caelestialium, Stenotus rubrovittatus, Lygus lineolaris, or Blissus leucopterus leucopterus (Chinchi bug));

Aleyrodidae (for example, Trialeurodes vaporariorum, Bemisia tabaci, Dialeurodes citri, or Aleurocanthus spiniferus);

Coccoidea (for example, Aonidiella aurantii, Comstockaspis perniciosa, Unaspis citri, Ceroplastes rubens, Icerya purchasi, Planococcus kraunhiae, Pseudococcus longispinis, Pseudaulacaspis pentagona, or Brevennia rehi);

Psyllidae (for example, Diaphorina citri, Psylla pyrisuga, or Bactericerca cockerelli);

Tingidae (for example, Stephanitis nasi);

Cimicidae (for example, Cimex lectularius);

Quesada gigas (Giant Cicada);

and the others.

Lepidoptera Pests:

Pyralidae (for example, Chilo suppressalis, Chilo polychrysus (Darkheaded stem borer), Tryporyza incertulas, Chilo polychrysus, Scirpophaga innotata, Scirpophaga incertulas (Yellow stem borer), Sesamia inferens (Pink borer), Rupela albinella, Cnaphalocrocis medinalis, Marasmia patnalis, Marasmia exigna, Notarcha derogata, Plodia interpunctella, Ostrinia furnacalis, Hellula undalis, Pediasia teterrellus, Nymphula depunctalis, Marasmia spp., Hydraecia immanis (Hop vine borer), Ostrinia nubilalis (European corn borer), Elasmopalpus lignosellus (Lesser cornstalk borer), Epinotia aporema (Bean Shoot Borer), Diatraea saccharalis (Sugarcane borer), or Telchin licus (Giant Sugarcane borer));

Noctuidae (for example, Spodoptera litura, Spodoptera exigua, Pseudaletia separata, Mamestra brassicae, Sesamia inferens, Spodoptera mauritia, Spodoptera frugiperda, Spodoptera exempta, Agrotis ipsilon, Plusia nigrisigna, Pseudoplusia includens (Soybean looper), Trichoplusia spp., Heliothis spp. (for example, Heliothis virescens), Helicoverpa spp. (for example, Helicoverpa armigera), Anticarsia gammatalis (Velvetbean caterpillar), or Alabama argillacea (Cotton leafworm));

Pieridae (for example, Pieris rapae);

Tortricidae (for example, Adoxophyes spp., Grapholita molesta, Leguminivora glycinivorella, Matsumuraeses azukivora, Adoxophyes orana fasciata, Adoxophyes honmai, Homona magnanima, Archips fuscocupreanus, or Cydia pomonella);

Gracillariidae (for example, Caloptilia theivora or Phyllonorycter ringoneella);

Carposinidae (for example, Carposina niponensis or Ecdytolopha aurantiana (Citrus fruit borer));

Lyonetiidae (for example, Leucoptera coffeela (Coffee Leaf miner) or Lyonetia spp.);

Lymantriidae (for example, Lymantria spp. or Euproctis spp.);

Yponomeutidae (for example, Plutella xylostella);

Gelechiidae (for example, Pectinophora gossypiella or Phthorimaea operculella);

Arctiidae (for example, Hyphantria cunea);

and the others.

Thysanoptera Pests:

Thripidae (for example, Frankliniella occidentalis, Thrips parmi, Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa, Frankliniella occidentalis, Haplothrips aculeatus, or Stenchaetothrips biformis);

and the others.

Diptera Pests:

House mosquitoes (Culex spp.) (for example, Culex pipiens pallens, Culex tritaeniorhynchus, or Culex quinquefasciatus);

Aedes spp. (for example, Aedes aegypti or Aedes albopictus);

Anopheles spp. (for example, Anopheles sinensis);

Chironomidae;

Muscidae (for example, Musca domestica or Muscina stabulans);

Anthomyiidae (for example, Delia platura, Delia antiqua, or Tetanops myopaeformis);

Agromyzidae (for example, Agromyza oryzae, Hydrellia griseola, Liriomyza sativae, Liriomyza trifolii, or Chromatomyia horticola);

Chloropidae (for example, Chlorops oryzae);

Tephritidae (for example, Dacus cucurbitae or Ceratitis capitata);

Ephydridae (for example, Hydrellia philippina or Hydrellia sasakii);

Drosophilidae;

Phoridae (for example, Megaselia spiracularis);

Psychodidae (for example, Clogmia albipunctata);

Sciaridae;

Cecidomyiidae (for example, Mayetiola destructor or Orseolia oryzae);

Diopsidae (for example, Diopsis macrophthalma);

Tipulidae (for example, Tipula oleracea (Common cranefly) or Tipula paludosa (European cranefly));

and the others.

Coleoptera Pests:

Chrysomelidae (for example, Diabrotica virgifera virgifera, Diabrotica undecimpunctata howardi, Diabrotica barberi, Diabrotica virgifera zeae, Diabrotica balteata LeConte, Diabrotica speciosa, Diabrotica speciosa (Cucurbit Beetle), Cerotoma trifurcata, Oulema melanopus, Aulacophora femoralis, Phyllotreta striolata, Leptinotarsa decemlineata, Oulema oryzae, Colaspis brunnea, Chaetocnema pulicaria, Epitrix cucumeris, Dicladispa armigera, Stenolophus lecontei (Seedcorn beetle), or Clivinia impressifrons (Slender seedcorn beetle));

Scarabaeidae (for example, Anomala cuprea, Anomala rufocuprea, Popillia japonica, Rhizotrogus majalis (European Chafer), Bothynus gibbosus (carrot beetle), Colaspis brunnea (Grape Colaspis), yochrous denticollis (southern Corn leaf beetle), Holotrichia spp., or Phyllophaga spp. (for example, Phyllophaga crinita));

Erirhinidae (for example, Sitophilus zeamais, Echinocnemus squameus, Lissorhoptrus oryzophilus, or Sphenophorus venatus);

Curculionidae (for example, Anthonomus grandis, Sphenophorus callosus (Southern Corn Billbug), Sternechus subsignatus (Soybean stalk weevil), or Sphenophorus spp. (for example, Sphenophorus levis));

Epilachna (for example, Epilachna vigintioctopunctata);

Scolytidae (for example, Lyctus brunneus or Tomicus piniperda);

Bostrychidae;

Ptinidae;

Cerambycidae (for example, Anoplophora malasiaca or Migdolus fryanus);

Elateridae (Agriotes sp., Aelous sp., Anchastus sp., Melanotus sp., Limonius sp., Conoderus sp., Ctenicera sp.) (for example, Melanotus okinawensis, Agriotes ogurae fuscicollis, or Melanotus legatus);

Staphylinidae (for example, Paederus fuscipes);

Hypothenemus hampei (Coffee Barry Borer);

and the others.

Orthoptera Pests:

Locusta migratoria, Gryllotalpa africana, Dociostaurus maroccanus, Chortoicetes terminifera, Nomadacris septemfasciata, Locustana pardalina (Brown Locust), Anacridium melanorhodon (Tree Locust), Calliptamus italicus (Italian Locust), Melanoplus differentialis (Differential grasshopper), Melanoplus bivittatus (Twostriped grasshopper), Melanoplus sanguinipes (Migratory grasshopper), Melanoplus femurrubrum (Red-Legged grasshopper), Camnula pellucida (Clearwinged grasshopper), Schistocerca gregaria, Gastrimargus musicus (Yellow-winged locust), Austracris guttulosa (Spur-throated locust), Oxya yezoensis, Oxya japonica, Patanga succincta, or Gryllidae (for example, Acheta domesticus, Teleogryllus emma, or Anabrus simplex (Mormon cricket));

and the others.

Hymenoptera Pests:

Tenthredinidae (for example, Athalia rosae or Athalia japonica);

Solenopsis spp.;

Attini spp. (for example, Atta capiguara (Brown leaf-cutting ant));

and the others.

Blattodea Pests:

Blattella germanica, Periplaneta fuliginosa, Periplaneta americana, Periplaneta brunnea, Blatta orientalis, and the others.

Termitidae Pests:

Reticulitermes speratus, Coptotermes formosanus, Incisitermes minor, Cryptotermes domesticus, Odontotermes formosanus, Neotermes koshunensis, Glyptotermes satsumensis, Glyptotermes nakajimai, Glyptotermes fuscus, Glyptotermes kodamai, Glyptotermes kushimensis, Hodotermopsis sjostedti, Coptotermes guangzhoensis, Reticulitermes amamianus, Reticulitermes miyatakei, Reticulitermes kanmonensis, Nasutitermes takasagoensis, Pericapritermes nitobei, Sinocapritermes mushae, Cornitermes cumulans, and the others.

Acarina Pests:

Tetranychidae (for example, Tetranychus urticae, Tetranychus kanzawai, Panonychus citri, Panonychus ulmi, Oligonychus spp., or Brevipalpus phoenicis (Southern Turkey spider mites));

Eriophyidae (for example, Aculops pelekassi, Phyllocoptruta citri, Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans, Eriophyes chibaensis, or Aculus schlechtendali);

Tarsonemidae (for example, Polyphagotarsonemus latus);

Tenuipalpidae (for example, Brevipalpus phoenicis);

Tuckerellidae;

Ixodidae (for example, Haemaphysalis longicornis, Haemaphysalis flava, Dermacentor taiwanicus, Dermacentor variabilis, Ixodes ovatus, Ixodes persulcatus, Ixodes scapularis, Amblyomma americanum, Boophilus microplus, or Rhipicephalus sanguineus);

Acaridae (for example, Tyrophagus putrescentiae or Tyrophagus similis);

Pyroglyphidae (for example, Dermatophagoides farinae or Dermatophagoides ptrenyssnus);

and the others.

The agent for controlling harmful arthropods of the present invention comprises the Present compound and an inert carrier. The agent for controlling harmful arthropods of the present invention is usually prepared by mixing the Present compound with an inert carrier such as solid carriers, liquid carriers, or gaseous carriers, and if necessary, adding surfactants and the other auxiliary agents for formulation, to formulate into emulsifiable concentrates, oil solutions, dust formulations, granules, wettable powders, flowables, microcapsules, aerosols, smoking agents, poison baits, resin formulations, shampoo formulations, paste-like formulations, foams, carbon dioxide formulations, tablets, or the others. Such formulations may be processed into and used as mosquito repellent coils, electric mosquito repellent mats, liquid mosquito formulations, smoking agents, fumigants, sheet formulations, spot-on formulations, or formulations for oral treatment. Also, the agent for controlling harmful arthropods of the present invention may be mixed with other pesticides, miticides, nematicides, fungicides, plant growth regulators, herbicides, or synergists.

The agent for controlling harmful arthropods of the present invention usually comprises 0.01 to 95% by weight of the Present compound.

Examples of the solid carriers to be used in the formulation include fine powders or granules of clays (for example, kaolin clay, diatomaceous earth, bentonite, Fubasami clay, or acid white clay), synthetic hydrated silicon oxides, talcs, ceramics, other inorganic minerals (for example, sericite, quartz, sulfur, active carbon, calcium carbonate, or hydrated silica), chemical fertilizers (for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, or ammonium chloride), and the others; as well as synthetic resins (for example, polyester resins such as polypropylene, polyacrylonitrile, polymethylmethacrylate, and polyethylene terephthalate; nylon resins such as nylon-6, nylon-11, and nylon-66; polyamide resins; polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymers, or the others).

Examples of the above-mentioned liquid carriers include water; alcohols (for example, methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, or phenoxy ethanol); ketones (for example, acetone, methyl ethyl ketone, or cyclohexanone); aromatic hydrocarbons (for example, toluene, xylene, ethyl benzene, dodecyl benzene, phenyl xylyl ethane, or methylnaphthalene); aliphatic hydrocarbons (for example, hexane, cyclohexane, kerosene, or light oil); esters (for example, ethyl acetate, butyl acetate, isopropyl myristate, ethyl oleate, diisopropyl adipate, diisobutyl adipate, or propylene glycol monomethyl ether acetate); nitriles (for example, acetonitrile or isobutyronitrile); ethers (for example, diisopropyl ether, 1,4-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, or 3-methoxy-3-methyl-1-butanol); acid amides (for example, DMF or dimethylacetamide); halogenated hydrocarbons (for example, dichloromethane, trichloroethane, or carbon tetrachloride); sulfoxides (for example, DMSO); propylene carbonate; and vegetable oils (for example, soybean oil or cottonseed oil).

Examples of the above-mentioned gaseous carriers include fluorocarbon, butane gas, liquefied petroleum gas (LPG), dimethyl ether, and carbon dioxide gas.

Examples of the surfactants include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, and polyethylene glycol fatty acid esters; and anionic surfactants such as alkyl sulfonates, alkylbenzene sulfonates, and alkyl sulfates.

Examples of the other auxiliary agents for formulation include binders, dispersants, colorants, and stabilizers. Specific examples thereof include casein, gelatin, saccharides (for example, starch, gum arabic, cellulose derivatives, or alginic acid), lignin derivatives, bentonite, water-soluble synthetic polymers (for example, polyvinyl alcohol, polyvinyl pyrrolidone, or polyacrylic acids), PAP (acidic isopropyl phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), and BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).

Examples of base material of the resin formulation include vinyl chloride polymers, polyurethane, and the others, and a plasticizer such as phthalic acid esters (for example, dimethyl phthalate or dioctyl phthalate), adipic acid esters, and stearic acid may be added to these base materials, if necessary. The resin formulation may be prepared by mixing the Present compound with the above-mentioned base material, kneading the mixture in a conventional kneading apparatus, followed by molding it by injection molding, extrusion molding, pressure molding, or the like. The resultant resin formulation may be subjected to further molding, cutting procedure, or the like, if necessary, to be processed into shapes such as a plate, film, tape, net, and string shape. These resin formulations may be processed into animal collars, animal ear tags, sheet products, trap strings, gardening supports, or other products.

Examples of the base material for the poison baits include bait ingredients such as grain powder, vegetable oil, saccharide, and crystalline cellulose, and if necessary, with addition of antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, preservatives such as dehydroacetic acid, accidental ingestion inhibitors for children and pets such as a chili powder, insect attraction fragrances such as cheese flavor, onion flavor, and peanut oil, or the other ingredient.

The method for controlling harmful arthropods of the present invention is conducted by applying an effective amount of the Present compound to a harmful arthropod directly and/or a habitat of pests (for example, plant bodies, soil, an interior of a house, or animal bodies). In the method for controlling harmful arthropods of the present invention, the Present compound is usually used in the form of an agent for controlling harmful arthropods of the present invention.

When an agent for controlling harmful arthropods of the present invention is used for controlling pests in an agricultural field, the application dose as an amount of the Present compound is usually within a range from 1 to 10,000 g per 10,000 m². The emulsifiable concentrate, the wettable powder, or the flowable formulation etc. of an agent for controlling harmful arthropods of the present invention is usually applied by diluting it with water in such a way that a concentration of the active ingredient is within a range from 0.01 to 10,000 ppm. The granular formulation or the dust formulation etc., is usually applied as itself without diluting it.

These formulations and diluents of the formulations with water may be directly sprayed to a harmful arthropod or a plant such as a crop to be protected from a harmful arthropod, or applied to a soil in a cultivated area to control a pest that inhabits the soil.

Also, a resin formulation processed into sheet shape or string shape may be wrapped around a crop, stretched near a crop, spread on a plant foot soil, or the like.

When the agent for controlling harmful arthropods of the present invention is used to control pests that live inside a house, the application dose as an amount of the Present compound is usually within a range from 0.01 to 1,000 mg per 1 m² of an area to be treated, in the case of using it on a planar area. In the case of using it spatially, the application dose as an amount of the Present compound is usually within a range from 0.01 to 500 mg per 1 m³ of the space to be treated. When the agent for controlling harmful arthropods of the present invention is formulated into emulsifiable concentrates, wettable powders, flowables, or the others, such formulations are usually applied after diluting it with water in such a way that a concentration of the active ingredient is within a range from 0.1 to 10,000 ppm, and then sparging it. In the case of being formulated into oil solutions, aerosols, smoking agents, poison baits, or the others, such formulations are used as itself without diluting it.

When the agent for controlling harmful arthropods of the present invention is used for controlling external parasites of livestock such as cows, horses, pigs, sheep, goats, and chickens, and small animals such as dogs, cats, rats, and mice, the agent of the present invention may be applied to the animals by a known method in the veterinary field. Specifically, when systemic control is intended, the agent of the present invention is administered to the animals as a tablet, a mixture with feed, or a suppository, or by injection (including intramuscular, subcutaneous, intravenous, and intraperitoneal injections), or the like. On the other hand, when non-systemic control is intended, the agent of the present invention is applied to the animals by means of spraying of the oil solution or aqueous solution, pour-on or spot-on treatment, or washing of the animal with a shampoo formulation, or by putting a collar or ear tag made of the resin formulations to the animal, or the like. In the case of administering to an animal body, the dose of the Present compound is usually within a range from 0.1 to 1,000 mg per 1 kg of an animal body weight.

EXAMPLES

The following Examples including Preparation examples, Formulation examples, and Test examples serve to illustrate the present invention more in detail, which should not intend to limit the present invention.

First, regarding the preparation of the Present compound, the Preparation Examples are shown below.

Preparation Example 1

To a mixture of 2-bromo-5-(2,2,3,3,3-pentafluoropropoxy)pyridine (hereinafter referred to as “Intermediate compound 1”) (2.1 g), 2-[2-(ethylsulfanyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolan (hereinafter referred to as “Intermediate compound 2”) (1.0 g), a 2 M sodium carbonate aqueous solution (4.7 mL), and 1,2-dimethoxyethane (11 mL) was added tetrakistriphenylphosphinepalladium(0) (220 mg) under nitrogen atmosphere at room temperature. The resulting mixture was stirred at 80° C. for 3 hours. The resulting reaction mixture was allowed to stand to room temperature, and then to the mixture was added water, and the mixture was extracted with ethyl acetate. The resulting organic layers were washed with saturated brine and dried over anhydrous sodium sulfate, and the organic layers were concentrated under reduced pressure. The resulting residues were subjected to silica gel chromatography to give the Present compound 1 represented by the following formula (1.0 g).

The compounds prepared according to the process described in the Preparation Example 1 and the physical properties thereof are shown below.

The compounds represented by formula (I-1)

[wherein the number on the benzene ring represents the binding position of each substituent.] wherein R¹, (R³)_(q), and n represent any one combination indicated in Table 6.

TABLE 6 Present compound R¹ (R³)_(q) n 1 CF₃CF₂CH₂ H 0 4 CF₂HCF₂CH₂ H 0 Present Compound 1

¹H-NMR (CDCl₃) δ: 8.45 (1H, d), 7.57 (1H, dd), 7.42 (2H, td), 7.37-7.32 (2H, m), 7.28-7.23 (1H, m), 4.53 (2H, td), 2.85 (2H, q), 1.24 (3H, t).

Present Compound 4

1H-NMR (CDCl₃) δ: 8.45 (1H, dd), 7.57 (1H, dd), 7.45-7.40 (2H, m), 7.37-7.31 (2H, m), 7.28-7.24 (1H, m), 6.25-5.95 (1H, m), 4.47 (2H, tt), 2.85 (2H, q), 1.24 (3H, t).

Preparation Example 2

To a suspension of sodium hydride (60%, oily) (1.2 g) and DMSO (24 mL) was added dropwise ethanethiol (2.1 mL) under ice-cooling. The resulting mixture was stirred under ice-cooling for 10 minutes, and then to the reaction mixture was added dropwise a mixed solution of 1-bromo-4-chloro-2-fluorobenzene (5.0 g) and DMSO (10 mL). The resulting reaction mixture was stirred at 100° C. for 2 hours. The resulting reaction mixture was allowed to stand to room temperature, and then to the mixture was added water, and the mixture was extracted with MTBE. The resulting organic layers were dried over anhydrous sodium sulfate, and the organic layers were concentrated under reduced pressure. The resulting residues were subjected to silica gel chromatography to give the Intermediate compound 5 represented by the following formula (5.47 g).

The compounds prepared according to the process described in the Preparation Example 2 and the physical properties thereof are shown below.

The compounds represented by formula (B-1)

[wherein the number on the benzene ring represents the binding position of each substituent.] wherein R⁴¹ and (R³)_(q) represent any one combination indicated in Table 7, provided that Bn represents a benzyl group.

TABLE 7 Intermediate compound R⁴¹ (R³)_(q) 5 Br 4-Cl 6 Br 5-Cl 7 Br 3-Cl 12

4-CF₃ Intermediate Compound 5

¹H-NMR (CDCl₃) δ: 7.44 (1H, d), 7.14 (1H, d), 6.98 (1H, dd), 2.97 (2H, q), 1.40 (3H, t).

Intermediate Compound 6

¹H-NMR (CDCl₃) δ: 7.56 (1H, d), 7.25 (1H, dd), 7.15 (1H, d), 2.95 (2H, q), 1.37 (3H, t).

Intermediate Compound 7

¹H-NMR (CDCl₃) δ: 7.58 (1H, dd), 7.43 (1H, dd), 7.09 (1H, t), 2.96 (2H, q), 1.24 (3H, t).

Intermediate Compound 12

¹H-NMR (CDCl₃) δ: 8.50 (1H, dd), 7.59-7.33 (10H, m), 5.17 (2H, s), 2.90 (2H, q), 1.28 (3H, t).

The compounds prepared according to the process described in the Preparation Example 2 and the physical properties thereof are shown below.

The compounds represented by formula (I-2)

[wherein the number on the benzene ring represents the binding position of each substituent.] wherein R¹ and (R³)_(q) represent any one combination indicated in Table 8.

TABLE 8 Present compound R¹ (R³)_(q) 15 CF₃CF₂CH₂ 4-OCH₃ 25 CF₃CF₂CH₂ 3-CF₃ 71 CF₃CF₂CH₂ 4-CF₃ 72 CF₃CF₂CH₂ 6-Cl 73 CF₃CF₂CH₂ 6-CF₃ 31 CF₃CF₂CH₂ 4-NO₂ 47 CF₃CF₂CH₂ 4-OCF₃ 74 CF₃CF₂CH₂ 3-Me 56 CF₃CF₂CH₂ 4-Br 75 CF₃CF₂CH₂ 5-OCF₃ 76 CF₃CF₂CH₂ 5-NO₂ 64 CF₃CF₂CH₂ 5-CN 77 CF₃CF₂CH₂ 3-OMe Present Compound 15

¹H-NMR (CDCl₃) δ: 8.43 (1H, d), 7.54 (1H, d), 7.38 (1H, d), 7.31 (1H, dd), 6.94 (1H, d), 6.78 (1H, dd), 4.52 (2H, t), 3.86 (3H, s), 2.85 (2H, q), 1.25 (3H, t).

Present Compound 25

¹H-NMR (CDCl₃) δ: 8.44 (1H, d), 7.78-7.75 (2H, m), 7.67-7.64 (1H, m), 7.53-7.48 (1H, m), 7.35 (1H, dd), 4.55 (2H, td), 2.32 (2H, q), 0.93 (3H, t).

Present Compound 71

¹H-NMR (CDCl₃) δ: 8.47 (1H, dd), 7.60-7.47 (4H, m), 7.37 (1H, dd), 4.54 (2H, td), 2.91 (2H, q), 1.28 (3H, t).

Present Compound 72

¹H-NMR (CDCl₃) δ: 8.49 (1H, d), 7.43-7.28 (4H, m), 7.12-7.08 (1H, m), 4.54 (2H, t), 2.83 (2H, d), 1.25 (3H, t).

Present Compound 73

¹H-NMR (CDCl₃) δ: 8.46 (1H, dd), 7.52-7.44 (2H, m), 7.39-7.34 (3H, m), 4.54 (2H, t), 2.86 (2H, dd), 1.26 (3H, t).

Present Compound 31

¹H-NMR (CDCl₃) δ: 8.49 (1H, d), 8.20 (1H, d), 8.05 (1H, dd), 7.62 (1H, d), 7.59 (1H, d), 7.39 (1H, dd), 4.55 (2H, td), 2.99 (2H, q), 1.33 (3H, t).

Present Compound 47

¹H-NMR (CDCl₃) δ: 8.45 (1H, d), 7.55 (1H, d), 7.44 (1H, d), 7.35 (1H, dd), 7.20-7.18 (1H, m), 7.10-7.07 (1H, m), 4.53 (2H, t), 2.88 (2H, q), 1.28 (3H, t).

Present Compound 74

378 (M+H)

Present Compound 56

¹H-NMR (CDCl₃) δ: 8.44 (1H, d), 7.54 (1H, d), 7.48 (1H, d), 7.38-7.32 (2H, m), 7.29 (1H, d), 4.53 (2H, td), 2.87 (2H, q), 1.26 (3H, td).

Present Compound 75

¹H-NMR (CDCl₃) δ: 8.46 (1H, dd), 7.59 (1H, dd), 7.41 (1H, d), 7.35 (1H, dd), 7.33-7.32 (1H, m), 7.23-7.19 (1H, m), 4.54 (2H, td), 2.84 (2H, q), 1.24 (3H, t).

Present Compound 76

¹H-NMR (CDCl₃) δ: 8.49 (1H, t), 8.27 (1H, d), 8.19 (1H, dd), 7.60 (1H, dd), 7.43-7.38 (2H, m), 4.56 (2H, td), 3.01 (2H, q), 1.35 (3H, t).

Present Compound 64

¹H-NMR (CDCl₃) δ: 8.47 (1H, dd), 7.67-7.66 (1H, m), 7.59 (1H, dd), 7.55 (1H, dd), 7.40-7.36 (2H, m), 4.55 (2H, td), 2.95 (2H, q), 1.32 (3H, t).

Present Compound 77

¹H-NMR (CDCl₃) δ: 8.41 (1H, d), 7.49 (1H, d), 7.36 (1H, t), 7.32 (1H, dd), 7.10 (1H, dd), 6.96 (1H, dd), 4.53 (2H, t), 3.95 (3H, s), 2.68 (2H, q), 1.00 (3H, t).

Preparation Example 3

To a mixture of the Intermediate compound 5 (2.0 g), triisopropyl borate (2.4 mL), toluene (20 mL), and THE (6.6 mL) was added dropwise a 2.6 M n-butyllithium solution in hexane (4 mL) under nitrogen atmosphere at −78° C. The reaction mixture was stirred at −78° C. for 1 hour and then allowed to stand to room temperature, and to the mixture were added a 2 M sodium carbonate aqueous solution (12 mL) and the Intermediate compound 1 (2.3 g). To the mixture was added tetrakistriphenylphosphinepalladium(0) (920 mg), and then the mixture was stirred at 95° C. for 6 hours. The resulting reaction mixture was allowed to stand to room temperature, and to the mixture was added water, and the mixture was extracted with ethyl acetate. The resulting organic layers were dried over anhydrous sodium sulfate, and the organic layers were concentrated under reduced pressure. The resulting residues were subjected to silica gel chromatography to give the Present compound 12 represented by the following formula (2.4 g).

The compounds prepared according to the process described in the Preparation Example 3 and the physical properties thereof are shown below.

The compounds represented by formula (I-2)

[wherein the number on the benzene ring represents the binding position of each substituent.] wherein R¹ and (R³)_(q) represent any one combination indicated in Table 9.

TABLE 9 Present compound R¹ (R³)_(q) 12 CF₃CF₂CH₂ 4-Cl 21 CF₃CF₂CH₂ 5-Cl 28 CF₃CF₂CH₂ 3-Cl 50 CF₃CF₂CH₂ 4-Me 44 CF₃CF₂CH₂ 5-Me 78 CF₃CF₂CH₂ 6-Me 35 CF₃CF₂CH₂ 6-OMe Present Compound 12

¹H-NMR (CDCl₃) δ: 8.44 (1H, d), 7.54 (1H, d), 7.37-7.32 (3H, m), 7.21 (1H, dd), 4.52 (2H, td), 2.87 (2H, q), 1.27 (3H, t).

Present Compound 21

¹H-NMR (CDCl₃) δ: 8.45 (1H, d), 7.57 (1H, d), 7.44 (1H, t), 7.36-7.31 (3H, m), 4.53 (2H, t), 2.82 (2H, q), 1.22 (3H, t).

Present Compound 28

¹H-NMR (CDCl₃) δ: 8.41 (1H, dd), 7.55-7.50 (2H, m), 7.40-7.30 (3H, m), 4.54 (2H, td), 2.63 (2H, q), 1.00 (3H, t).

Present Compound 50

¹H-NMR (CDCl₃) δ: 8.44 (1H, dd), 7.55 (1H, dd), 7.34-7.30 (2H, m), 7.22 (1H, s), 7.07-7.05 (1H, m), 4.52 (2H, td), 2.83 (2H, q), 2.39 (3H, s), 1.23 (3H, t).

Present Compound 44

¹H-NMR (CDCl₃) δ: 8.44 (1H, d), 7.58 (1H, d), 7.35-7.31 (2H, m), 7.28 (1H, d), 7.18-7.15 (1H, m), 4.52 (2H, t), 2.77 (2H, q), 2.36 (3H, s), 1.19 (3H, t).

Present Compound 78

¹H-NMR (CDCl₃) δ: 8.47 (1H, d), 7.36 (1H, dd), 7.29-7.20 (3H, m), 7.09 (1H, dt), 4.54 (2H, t), 2.79 (2H, q), 2.04 (3H, s), 1.22 (3H, t).

Present Compound 35

¹H-NMR (CDCl₃) δ: 8.47 (1H, dd), 7.36-7.29 (3H, m), 6.99 (1H, dd), 6.80 (1H, dd), 4.52 (2H, td), 3.72 (3H, s), 2.82 (2H, q), 1.23 (3H, t).

The compound prepared according to the process described in the Preparation Example 3 and the physical property thereof are shown below.

The compound represented by formula (I-3)

[wherein the number on the benzene ring represents the binding position of each substituent.] wherein R¹ represents a CF₃CF₂CH₂ group, X represents a fluorine atom, and (R³)_(q) represents a 4-OCF₃ group (Intermediate compound 18). Intermediate Compound 18

¹H-NMR (CDCl₃) δ: 8.47 (1H, d), 8.03 (1H, t), 7.80-7.77 (1H, m), 7.35 (1H, dd), 7.15-7.13 (1H, m), 7.08-7.05 (1H, m), 4.53 (2H, t).

Preparation Example 4

To a mixed solution of the Present compound 1 (0.72 g) and ethyl acetate (5 mL) was added dropwise a mixture of mCPBA (70%) (0.68 g) and ethyl acetate (1.7 mL) under ice-cooling. The mixture was stirred under ice-cooling for 4 hours, and then to the mixture were sequentially added a saturated sodium thiosulfate aqueous solution and a saturated sodium hydrogen carbonate aqueous solution, and the mixture was extracted with ethyl acetate. The resulting organic layers were dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residues were subjected to silica gel chromatography to give the Present compound 2 represented by the following formula (0.23 g) and the Present compound 3 represented by the following formula (0.41 g).

The compounds prepared according to the process described in the Preparation Example 4 and the physical properties thereof are shown below.

The compounds represented by formula (I-1)

[wherein the number on the benzene ring represents the binding position of each substituent.] wherein R¹, (R³)_(q), and n represent any one combination indicated in Table 10.

TABLE 10 Present compound R¹ (R³)_(q) n 2 CF₃CF₂CH₂ H 1 3 CF₃CF₂CH₂ H 2 5 CF₂HCF₂CH₂ H 1 6 CF₂HCF₂CH₂ H 2 13 CF₃CF₂CH₂ 4-Cl 1 14 CF₃CF₂CH₂ 4-Cl 2 16 CF₃CF₂CH₂ 4-OCH₃ 1 17 CF₃CF₂CH₂ 4-OCH₃ 2 19 CF₃CF₂CH₂ 5-CF₃ 1 20 CF₃CF₂CH₂ 5-CF₃ 2 22 CF₃CF₂CH₂ 5-Cl 1 23 CF₃CF₂CH₂ 5-Cl 2 26 CF₃CF₂CH₂ 3-CF₃ 1 27 CF₃CF₂CH₂ 3-CF₃ 2 29 CF₃CF₂CH₂ 3-Cl 1 30 CF₃CF₂CH₂ 3-Cl 2 41 CF₃CF₂CH₂ 4-CF₃ 1 39 CF₃CF₂CH₂ 6-CF₃ 2 52 CF₃CF₂CH₂ 4-Me 2 51 CF₃CF₂CH₂ 4-Me 1 46 CF₃CF₂CH₂ 5-Me 2 45 CF₃CF₂CH₂ 5-Me 1 37 CF₃CF₂CH₂ 6-OMe 2 36 CF₃CF₂CH₂ 6-OMe 1 43 CF₃CF₂CH₂ 6-Me 2 32 CF₃CF₂CH₂ 4-NO₂ 2 49 CF₃CF₂CH₂ 4-OCF₃ 2 48 CF₃CF₂CH₂ 4-OCF₃ 1 42 CF₃CF₂CH₂ 6-Cl 2 40 CF₃CF₂CH₂ 3-Me 2 58 CF₃CF₂CH₂ 4-Br 2 57 CF₃CF₂CH₂ 4-Br 1 55 CF₃CF₂CH₂ 5-OCF₃ 2 54 CF₃CF₂CH₂ 5-OCF₃ 1 34 CF₃CF₂CH₂ 5-NO₂ 2 33 CF₃CF₂CH₂ 5-NO₂ 1 66 CF₃CF₂CH₂ 5-CN 2 65 CF₃CF₂CH₂ 5-CN 1 38 CF₃CF₂CH₂ 3-OMe 2 Present Compound 2

¹H-NMR (CDCl₃) δ: 8.40 (1H, d), 8.26 (1H, dd), 7.71 (1H, d), 7.67-7.61 (2H, m), 7.58-7.53 (1H, m), 7.40 (1H, dd), 4.55 (2H, td), 3.48-3.38 (1H, m), 2.92-2.83 (1H, m), 1.40 (3H, t).

Present Compound 3

¹H-NMR (CDCl₃) δ: 8.37 (1H, d), 8.16 (1H, dd), 7.70 (1H, td), 7.61 (1H, td), 7.48 (1H, dd), 7.44 (1H, dd), 7.36 (1H, dd), 4.53 (2H, td), 3.44 (2H, q), 1.27 (3H, t).

Present Compound 5

¹H-NMR (CDCl₃) δ: 8.40 (1H, d), 8.25 (1H, dd), 7.70 (1H, d), 7.67-7.61 (2H, m), 7.55 (1H, td), 7.39 (1H, dd), 6.23-5.94 (1H, m), 4.49 (2H, t), 3.48-3.38 (1H, m), 2.92-2.82 (1H, m), 1.39 (3H, t).

Present Compound 6

¹H-NMR (CDCl₃) δ: 8.35 (1H, dd), 8.15 (1H, dd), 7.69 (1H, td), 7.61 (1H, td), 7.48 (1H, dd), 7.44 (1H, dd), 7.35 (1H, dd), 6.23-5.94 (1H, m), 4.46 (2H, dd), 3.44 (2H, q), 1.27 (3H, t).

Present Compound 13

¹H-NMR (CDCl₃) δ: 8.40 (1H, d), 8.24 (1H, d), 7.70 (1H, d), 7.62 (1H, d), 7.51 (1H, dd), 7.40 (1H, dd), 4.55 (2H, td), 3.50-3.40 (1H, m), 2.92-2.83 (1H, m), 1.41 (3H, t).

Present Compound 14

¹H-NMR (CDCl₃) δ: 8.36 (1H, dd), 8.15 (1H, d), 7.66 (1H, dd), 7.46 (1H, dd), 7.39 (1H, d), 7.36 (1H, dd), 4.53 (2H, td), 3.47 (2H, q), 1.29 (3H, t).

Present Compound 16

¹H-NMR (CDCl₃) δ: 8.36 (1H, d), 7.81 (1H, d), 7.64 (1H, d), 7.61 (1H, d), 7.37 (1H, dd), 7.06 (1H, dd), 4.53 (2H, td), 3.95 (3H, s), 3.49-3.39 (1H, m), 2.88-2.79 (1H, m), 1.41 (3H, t).

Present Compound 17

¹H-NMR (CDCl₃) δ: 8.35 (1H, d), 7.67 (1H, d), 7.45 (1H, d), 7.38-7.32 (2H, m), 7.19 (1H, dd), 4.52 (2H, dd), 3.92 (3H, s), 3.43 (2H, q), 1.26 (3H, t).

Present Compound 19

¹H-NMR (CDCl₃) δ: 8.44-8.43 (1H, m), 8.41 (1H, d), 7.92 (1H, br s), 7.89-7.86 (1H, m), 7.80-7.77 (1H, m), 7.44 (1H, dd), 4.57 (2H, td), 3.52-3.42 (1H, m), 2.95-2.85 (1H, m), 1.41 (3H, t).

Present Compound 20

¹H-NMR (CDCl₃) δ: 8.39-8.38 (1H, m), 8.30 (1H, d), 7.87 (1H, dd), 7.71-7.70 (1H, m), 7.52 (1H, dd,), 7.40 (1H, dd), 4.54 (2H, td), 3.49 (2H, q), 1.29 (3H, t).

Present Compound 22

¹H-NMR (CDCl₃) δ: 8.41 (1H, t), 8.20 (1H, dd), 7.71 (1H, dd), 7.65 (1H, t), 7.60 (1H, dt), 7.41 (1H, dt), 4.56 (2H, t), 3.48-3.38 (1H, m), 2.93-2.83 (1H, m), 1.39 (3H, t).

Present Compound 23

¹H-NMR (CDCl₃) δ: 8.37 (1H, dd), 8.09 (1H, d), 7.58 (1H, dd), 7.48 (1H, dd), 7.44 (1H, d), 7.37 (1H, dd), 4.53 (2H, td), 3.44 (2H, q), 1.26 (3H, t).

Present Compound 26

¹H-NMR (CDCl₃) δ: 8.36 (1H, d), 7.86-7.83 (1H, m), 7.64 (1H, t), 7.56-7.53 (1H, m), 7.49-7.45 (1H, m), 7.34 (1H, dd), 4.53 (2H, td), 3.82-3.73 (1H, m), 3.10-3.00 (1H, m), 1.32 (3H, t).

Present Compound 27

¹H-NMR (CDCl₃) δ: 8.32-8.31 (1H, m), 8.00-7.96 (1H, m), 7.76 (1H, t), 7.61-7.58 (1H, m), 7.47-7.44 (1H, m), 7.38 (1H, dd), 4.53 (2H, td), 3.78-3.68 (2H, br m), 1.38 (3H, t).

Present Compound 29

¹H-NMR (CDCl₃) δ: 8.36 (1H, d), 7.50 (2H, dd), 7.44 (1H, t), 7.36-7.33 (2H, m), 4.56-4.50 (2H, m), 3.82-3.73 (1H, m), 3.46-3.36 (1H, m), 1.43 (3H, t).

Present Compound 30

¹H-NMR (CDCl₃) δ: 8.32 (1H, d), 7.63 (1H, dd), 7.54 (1H, t), 7.39-7.36 (1H, m), 7.34-7.29 (2H, m), 4.51 (2H, t), 3.55 (2H, q), 1.35 (3H, t).

Present Compound 41

¹H-NMR (CDCl₃) δ: 8.56 (1H, s), 8.44 (1H, d), 7.82-7.79 (2H, m), 7.77 (1H, d), 7.44 (1H, dd), 4.57 (2H, td), 3.53-3.43 (1H, m), 2.94-2.86 (1H, m), 1.42 (3H, t).

Present Compound 39

¹H-NMR (CDCl₃) δ: 8.38-8.37 (2H, m), 8.07 (1H, d), 7.77 (1H, dd), 7.43 (1H, d), 7.35 (1H, dd), 4.54 (2H, t), 3.28-3.13 (2H, m), 1.21 (3H, t).

Present Compound 52

¹H-NMR (CDCl₃) δ: 8.36-8.35 (1H, m), 7.96 (1H, s), 7.50-7.45 (2H, m), 7.36-7.31 (2H, m), 4.52 (2H, t), 3.43 (2H, dd), 2.50 (3H, s), 1.27 (3H, t).

Present Compound 51

¹H-NMR (CDCl₃) δ: 8.38 (1H, d), 8.05 (1H, d), 7.67 (1H, d), 7.56 (1H, d), 7.39-7.33 (2H, m), 4.54 (2H, td), 3.46-3.41 (1H, m), 2.86-2.82 (1H, m), 2.50 (3H, s), 1.40 (3H, t).

Present Compound 46

¹H-NMR (CDCl₃) δ: 8.36 (1H, dd), 8.02 (1H, d), 7.48 (1H, dd), 7.41-7.39 (1H, m), 7.35 (1H, dd), 7.25-7.23 (1H, m), 4.52 (2H, t), 3.37 (2H, q), 2.48 (3H, s), 1.24 (3H, t).

Present Compound 45

¹H-NMR (CDCl₃) δ: 8.39 (1H, dd), 8.12 (1H, d), 7.69 (1H, dd), 7.46-7.42 (2H, m), 7.39 (1H, dd), 4.54 (2H, t), 3.43-3.34 (1H, m), 2.89-2.80 (1H, m), 2.48 (3H, s), 1.37 (3H, t).

Present Compound 37

¹H-NMR (CDCl₃) δ: 8.37 (1H, d), 7.74 (1H, dd), 7.56 (1H, t), 7.39 (1H, d), 7.34 (1H, dd), 7.26 (1H, d), 4.52 (2H, t), 3.77 (3H, s), 3.22 (2H, d), 1.21 (3H, t).

Present Compound 36

¹H-NMR (CDCl₃) δ: 8.39 (1H, dd), 7.75 (1H, dd), 7.64-7.62 (1H, m), 7.59 (1H, t), 7.34 (1H, dd), 7.10 (1H, dd), 4.54 (2H, td), 3.83 (3H, s), 3.33-3.25 (1H, m), 2.86-2.77 (1H, m), 1.31 (3H, t).

Present Compound 43

¹H-NMR (CDCl₃) δ: 8.40 (1H, dd), 8.00-7.98 (1H, m), 7.57-7.56 (1H, m), 7.50 (1H, t), 7.37 (2H, d), 4.54 (2H, td), 3.10-3.02 (2H, m), 2.05 (3H, s), 1.17 (3H, t).

Present Compound 32

¹H-NMR (CDCl₃) δ: 9.02 (1H, d), 8.53 (1H, dd), 8.41 (1H, d), 7.67 (1H, d), 7.53 (1H, d), 7.41 (1H, dd), 4.55 (2H, t), 3.58 (2H, q), 1.33 (3H, t).

Present Compound 49

¹H-NMR (CDCl₃) δ: 8.37 (1H, dd), 8.03 (1H, d), 7.57-7.46 (3H, m), 7.38 (1H, dd), 4.53 (2H, td), 3.48 (2H, q), 1.28 (3H, t).

Present Compound 48

¹H-NMR (CDCl₃) δ: 8.41 (1H, d), 8.14 (1H, d), 7.73 (1H, d), 7.71 (1H, d), 7.43-7.38 (2H, m), 4.56 (2H, t), 3.50-3.40 (1H, m), 2.93-2.84 (1H, m), 1.39 (3H, t).

Present Compound 42

¹H-NMR (CDCl₃) δ: 8.40 (1H, d), 8.09-8.07 (1H, m), 7.78 (1H, dd), 7.56 (1H, t), 7.45-7.36 (2H, m), 4.54 (2H, t), 3.30-3.10 (2H, m), 1.21 (3H, t).

Present Compound 40

¹H-NMR (CDCl₃) δ: 8.28 (1H, dd), 7.48 (1H, t), 7.39-7.30 (3H), 7.18 (1H, dd), 4.50 (2H, td), 3.43 (2H, q), 2.78 (3H, s), 1.33 (3H, t).

Present Compound 58

¹H-NMR (CDCl₃) δ: 8.37 (1H, dd), 8.30 (1H, d), 7.82 (1H, dd), 7.46 (1H, dd), 7.36 (1H, dd), 7.32 (1H, d), 4.53 (2H, td), 3.47 (2H, q), 1.29 (3H, t).

Present Compound 57

¹H-NMR (CDCl₃) δ: 8.40-8.33 (2H, m), 7.70-7.60 (2H, m), 7.56-7.51 (1H, m), 7.43-7.38 (1H, m), 4.56 (2H, td), 3.50-3.40 (1H, m), 2.91-2.82 (1H, m), 1.41 (3H, t).

Present Compound 55

¹H-NMR (CDCl₃) δ: 8.38 (1H, d), 8.21 (1H, d), 7.49 (1H, dd), 7.45-7.41 (1H, m), 7.38 (1H, dd), 7.28-7.26 (1H, m), 4.54 (2H, t), 3.47 (2H, q), 1.28 (3H, t).

Present Compound 54

¹H-NMR (CDCl₃) δ: 8.42 (1H, d), 8.30 (1H, d), 7.71 (1H, d), 7.51-7.45 (2H, m), 7.42 (1H, dd), 4.56 (2H, t), 3.50-3.41 (1H, m), 2.94-2.85 (1H, m), 1.40 (3H, t).

Present Compound 34

¹H-NMR (CDCl₃) δ: 8.43-8.36 (3H, m), 8.30 (1H, d), 7.56 (1H, d), 7.42 (1H, dd), 4.55 (2H, t), 3.55 (2H, q), 1.31 (3H, t).

Present Compound 33

¹H-NMR (CDCl₃) δ: 8.56 (1H, d), 8.49-8.41 (3H, m), 7.88 (1H, d), 7.49 (1H, dd), 4.59 (2H, td), 3.56-3.47 (1H, m), 2.99-2.90 (1H, m), 1.43 (3H, t).

Present Compound 66

¹H-NMR (CDCl₃) δ: 8.39 (1H, d), 8.29 (1H, d), 7.89 (1H, dd), 7.75 (1H, d), 7.50 (1H, d), 7.40 (1H, dd), 4.54 (2H, t), 3.50 (2H, q), 1.29 (3H, t).

Present Compound 65

¹H-NMR (CDCl₃) δ: 8.45-8.43 (1H, m), 8.40 (1H, d), 7.97 (1H, d), 7.89 (1H, dd), 7.76 (1H, d), 7.45 (1H, dd), 4.57 (2H, td), 3.52-3.43 (1H, m), 2.94-2.85 (1H, m), 1.41 (3H, t).

Present Compound 38

¹H-NMR (CDCl₃) δ: 8.33 (1H, dd), 7.58 (1H, dd), 7.37 (1H, dd), 7.28 (1H, dd), 7.13 (1H, dd), 6.99 (1H, dd), 4.50 (2H, td), 4.03 (3H, s), 3.44-3.39 (2H, m), 1.26 (3H, t).

Preparation Example 5

To a mixed solution of the Present compound 28 (0.50 g) and ethyl acetate (3 mL) was added dropwise a mixture of mCPBA (70%) (1.2 g) and ethyl acetate (1.2 mL) under ice-cooling. The mixture was stirred under ice-cooling for 6 hours, and then to the mixture were sequentially added a saturated sodium thiosulfate aqueous solution and a saturated sodium hydrogen carbonate aqueous solution, and the mixture was extracted with ethyl acetate. The resulting organic layers were dried over sodium sulfate, and concentrated under reduced pressure. The resulting residues were subjected to silica gel chromatography to give the Present compound 10 represented by the following formula (0.33 g).

Present Compound 10

¹H-NMR (CDCl₃) δ: 8.03 (1H, d), 7.70 (1H, dd), 7.61 (1H, t), 7.27 (1H, d), 7.20 (1H, dd), 7.01 (1H, dd), 4.48 (2H, td), 4.04-3.97 (1H, m), 3.62-3.52 (1H, m), 1.43 (3H, t).

Preparation Example 6

To a mixture of the Intermediate compound 1 (1.0 g), 2-fluoro-4-methoxyphenylboronic acid (0.50 g), a 2 M sodium carbonate aqueous solution (4.4 mL), and 1,2-dimethoxyethane (9.8 mL) was added tetrakistriphenylphosphinepalladium(0) (340 mg) under nitrogen atmosphere at room temperature. The resulting mixture was stirred at 80° C. for 5 hours. The resulting reaction mixture was allowed to stand to room temperature, and to the mixture was added water, and the mixture was extracted with ethyl acetate. The resulting organic layers were dried over anhydrous sodium sulfate, and the organic layers were concentrated under reduced pressure. The resulting residues were subjected to silica gel chromatography to give the Intermediate compound 8 represented by the following formula (0.96 g).

The compounds prepared according to the process described in the Preparation Example 6 and the physical properties thereof are shown below.

The compounds represented by formula (C-1)

[wherein the number on the benzene ring represents the binding position of each substituent.] wherein R¹ and (R³)_(q) represent any one combination indicated in Table 11.

TABLE 11 Intermediate compound R¹ (R³)_(q) 8 CF₃CF₂CH₂ 4-OCH₃ 9 CF₃CF₂CH₂ 5-CF₃ 10 CF₃CF₂CH₂ 3-CF₃ 15 CF₃CF₂CH₂ 6-CF₃ 16 CF₃CF₂CH₂ 6-Cl 17 CF₃CF₂CH₂ 3-Me 19 CF₃CF₂CH₂ 4-NO₂ 22 CF₃CF₂CH₂ 5-OCF₃ 23 CF₃CF₂CH₂ 5-NO₂ 24 CF₃CF₂CH₂ 5-CN 25 CF₃CF₂CH₂ 3-OMe 26 CF₃CF₂CH₂ 4-CF₃ Intermediate Compound 8

¹H-NMR (CDCl₃) δ: 8.43 (1H, d), 7.90 (1H, t), 7.74 (1H, dt), 7.32 (1H, dd), 6.82 (1H, dd), 6.70 (1H, dd), 4.51 (2H, t), 3.85 (3H, s).

Intermediate Compound 9

¹H-NMR (CDCl₃) δ: 8.50 (1H, d), 8.33 (1H, dd), 7.85-7.82 (1H, m), 7.65-7.61 (1H, m), 7.36 (1H, dd), 7.30-7.25 (1H, m), 4.54 (2H, td).

Intermediate Compound 10

¹H-NMR (CDCl₃) δ: 8.49 (1H, d), 8.21-8.16 (1H, m), 7.84-7.81 (1H, m), 7.66-7.62 (1H, m), 7.38-7.34 (2H, m), 4.54 (2H, td).

Intermediate Compound 15

¹H-NMR (CDCl₃) δ: 8.46 (1H, dd), 7.60-7.49 (2H, m), 7.39-7.34 (3H, m), 4.54 (2H, td).

Intermediate Compound 16

¹H-NMR (CDCl₃) δ: 8.50 (1H, d), 7.43-7.29 (4H, m), 7.13-7.08 (1H, m), 4.54 (2H, t).

Intermediate Compound 17

¹H-NMR (CDCl₃) δ: 8.46 (1H, d), 7.76 (1H, dd), 7.70 (1H, td), 7.33 (1H, dd), 7.24-7.19 (1H, m), 7.14 (1H, t), 4.52 (2H, t), 2.35 (3H, s).

Intermediate Compound 19

¹H-NMR (CDCl₃) δ: 8.52 (1H, d), 8.26 (1H, t), 8.16-8.13 (1H, m), 8.05 (1H, dd), 7.93-7.90 (1H, m), 7.38 (1H, dd), 4.56 (2H, td).

Intermediate Compound 22

¹H-NMR (CDCl₃) δ: 8.48 (1H, d), 7.93-7.91 (1H, m), 7.85-7.83 (1H, m), 7.35 (1H, dd), 7.22-7.15 (2H, m), 4.54 (2H, td).

Intermediate Compound 23

¹H-NMR (CDCl₃) δ: 8.99 (1H, dd), 8.52 (1H, d), 8.26 (1H, ddd), 7.88-7.85 (1H, m), 7.38 (1H, dd), 7.32 (1H, dd), 4.56 (2H, td).

Intermediate Compound 24

¹H-NMR (CDCl₃) δ: 8.49 (1H, d), 8.41 (1H, dd), 7.85-7.82 (1H, m), 7.66 (1H, dq), 7.37 (1H, dd), 7.30-7.25 (1H, m), 4.55 (2H, t).

Intermediate Compound 25

¹H-NMR (CDCl₃) δ: 8.47 (1H, d), 7.80-7.77 (1H, m), 7.50-7.46 (1H, m), 7.34 (1H, dd), 7.20-7.15 (1H, m), 7.03-6.98 (1H, m), 4.53 (2H, td), 3.94 (3H, s).

Intermediate Compound 26

¹H-NMR (CDCl₃) δ: 8.50 (1H, d), 8.16-8.12 (1H, m), 7.86-7.83 (1H, m), 7.54-7.51 (1H, m), 7.45-7.42 (1H, m), 7.36 (1H, dd), 4.54 (2H, td).

Preparation Example 7

To a mixture of the Present compound 23 (0.40 g) and methanol (2 mL) was added sodium methoxide (0.27 g) under nitrogen atmosphere at room temperature. The resulting reaction mixture was stirred at 80° C. for 10 hours and then allowed to stand to room temperature, and to the mixture was added a saturated ammonium chloride aqueous solution at room temperature. The resulting mixture was extracted with ethyl acetate, and the organic layers were dried over anhydrous sodium sulfate. The resulting organic layers were concentrated under reduced pressure. The resulting residues were subjected to silica gel chromatography to give the Present compound 24 represented by the following formula (80 mg).

Present Compound 24

¹H-NMR (CDCl₃) δ: 8.35 (1H, t), 8.06 (1H, d), 7.46 (1H, dd), 7.35 (1H, dd), 7.05 (1H, dd), 6.90 (1H, d), 4.52 (2H, td), 3.89 (3H, s), 3.39 (2H, q), 1.24 (3H, t).

Preparation Example 8

The Present compound 18 represented by the following formula (1.5 g) was prepared by using the Intermediate compound 9 instead of l-bromo-4-chloro-2-fluorobenzene according to the process described in the Preparation Example 3.

Present Compound 18

¹H-NMR (CDCl₃) δ: 8.48 (1H, d), 7.66 (1H, d), 7.60-7.56 (2H, m), 7.44 (1H, d), 7.37 (1H, dd), 4.54 (2H, t), 2.94 (2H, q), 1.30 (3H, t).

Preparation Example 9

The Intermediate compound 11 represented by the following formula was prepared by using 2-(2-fluoro-4-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan instead of the Intermediate compound 2 and using 5-(benzyloxy)-2-chloropyridine instead of the Intermediate compound 1 according to the process described in the Preparation Example 1.

Intermediate Compound 11

¹H-NMR (CDCl₃) δ: 8.51 (1H, d), 8.13 (1H, t), 7.79 (1H, dd), 7.52-7.33 (8H, m), 5.18 (2H, s).

Preparation Example 10

The Intermediate compound 13 represented by the following formula (790 mg) was prepared by using the Intermediate compound 12 instead of the Present compound 1 according to the process described in the Preparation Example 4.

Intermediate Compound 13

¹H-NMR (CDCl₃) δ: 8.43 (1H, d), 8.40 (1H, d), 7.93 (1H, dd), 7.60 (1H, d), 7.49-7.36 (7H, m), 5.17 (2H, s), 3.51 (2H, q), 1.28 (3H, t).

Preparation Example 11

To a mixture of the Intermediate compound 13 (700 mg) and chloroform (25 mL) was added boron tribromide (a 2 M solution in dichloromethane) (2.8 mL) at −20° C. The resulting reaction mixture was stirred under ice-cooling for 1 hour. To the reaction mixture was added water, and the mixture was sequentially extracted with chloroform and ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residues were subjected to silica gel chromatography to give the Intermediate compound 14 represented by the following formula (430 mg).

Intermediate Compound 14

¹H-NMR (CDCl₃) δ: 8.43 (1H, d), 8.23 (1H, dd), 7.94 (1H, dd), 7.61 (1H, d), 7.37 (1H, d), 7.18 (1H, dd), 5.96 (1H, s), 3.60 (2H, q), 1.32 (3H, t).

Preparation Example 12

To a mixture of the Intermediate compound 14 (140 mg), cesium carbonate (170 mg), and NMP (3 mL) was added 2,2,2-trifluoroethyl=nonafluorobutylsulfonate (180 mg) under ice-cooling. The resulting reaction mixture was stirred at room temperature for 1.5 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The resulting organic layers were sequentially washed with water and saturated brine, and dried over anhydrous sodium sulfate. The organic layers were concentrated under reduced pressure to give the Present compound 7 represented by the following formula (150 mg).

The compounds prepared according to the process described in the Preparation Example 12 and the physical properties thereof are shown below.

The compounds represented by formula (I-1)

[wherein the number on the benzene ring represents the binding position of each substituent.] wherein R¹, (R³)_(q), and n represent any one combination indicated in Table 12.

TABLE 12 Present compound R¹ (R³)_(q) n 7 CF₃CH₂ 4-CF₃ 2 8 CF₃CF₂CH₂ 4-CF₃ 2 9 CF₃CFHCF₂CH₂ 4-CF₃ 2 11 CF₂HCF₂CH₂ 4-CF₃ 2 Present Compound 7

¹H-NMR (CDCl₃) δ: 8.43 (1H, d), 8.39 (1H, dd), 7.95 (1H, dd), 7.60 (1H, d), 7.50 (1H, dd), 7.39 (1H, dd), 4.48 (2H, q), 3.52 (2H, q), 1.30 (3H, t).

Present Compound 8

¹H-NMR (CDCl₃) δ: 8.43 (1H, d), 8.39 (1H, dd), 7.95 (1H, dd), 7.60 (1H, d), 7.50 (1H, dd), 7.39 (1H, dd), 4.54 (2H, td), 3.51 (2H, q), 1.30 (3H, t).

Present Compound 9

¹H-NMR (CDCl₃) δ: 8.43 (1H, d), 8.38 (1H, dd), 7.95 (1H, dd), 7.60 (1H, d), 7.50 (1H, dd), 7.39 (1H, dd), 5.32-5.10 (1H, m), 4.58-4.36 (2H, m), 3.51 (2H, q), 1.30 (3H, t).

Present Compound 11

¹H-NMR (CDCl₃) δ: 8.43 (1H, d), 8.38 (1H, d), 7.95 (1H, dd), 7.60 (1H, d), 7.50 (1H, d), 7.38 (1H, dd), 6.09 (1H, tt), 4.48 (2H, t), 3.52 (2H, q), 1.30 (3H, t).

Preparation Example 13

A mixture of the Present compound 32 (2.17 g), palladium carbon (10% palladium) (0.22 g), and ethyl acetate (12 mL) was stirred under hydrogen atmosphere at 35° C. for 6 hours. The resulting reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure to give the Present compound 53 represented by the following formula (2.00 g).

Present Compound 53

¹H-NMR (CDCl₃) δ: 8.33 (1H, d), 7.44-7.41 (2H, m), 7.31 (1H, dd), 7.21 (1H, d), 6.91 (1H, dd), 4.51 (2H, td), 4.03 (2H, br s), 3.42 (2H, q), 1.26 (3H, t).

The compounds prepared according to the process described in the Preparation Example 13 and the physical properties thereof are shown below.

Present Compound 62

¹H-NMR (CDCl₃) δ: 8.34 (1H, d), 7.88 (1H, d), 7.47-7.44 (1H, m), 7.33 (1H, dd), 6.74 (1H, dd), 6.59 (1H, d), 4.51 (2H, td), 4.21 (2H, br s), 3.30 (2H, q), 1.23 (3H, t).

Intermediate Compound 20

¹H-NMR (CDCl₃) δ: 8.40 (1H, d), 7.77 (1H, t), 7.70 (1H, dd), 7.29 (1H, dd), 6.56 (1H, dd), 6.44 (1H, dd), 4.50 (2H, td), 3.90 (2H, br s).

Preparation Example 14

To a mixture of the Present compound 53 (0.30 g) and pyridine (2 mL) was added cyclopropanecarbonyl chloride (0.11 mL) under ice-cooling. The resulting reaction mixture was stirred at room temperature for 3 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The resulting organic layers were sequentially washed with saturated potassium hydrogen sulfate, water, and saturated brine, and dried over anhydrous sodium sulfate. The organic layers were concentrated under reduced pressure to give the Present compound 63 represented by the following formula (0.35 g).

Present Compound 63

¹H-NMR (CDCl₃) δ: 8.37-8.34 (2H, m), 8.09 (1H, br s), 7.98 (1H, d), 7.46 (TH, dd), 7.41 (1H, d), 7.34 (1H, dd), 4.54-4.48 (2H, m), 3.56 (2H, q), 1.62-1.54 (1H, m), 1.30 (3H, t), 1.14-1.10 (2H, m), 0.91-0.88 (2H, m).

Preparation Example 15

A mixture of sodium nitrite (0.41 g) and (6.7 mL) was added to a mixture of the Intermediate compound 20 (8.58 g) and 48% hydrobromic acid (6.7 mL) under ice-cooling. The resulting reaction mixture was stirred at room temperature for 15 minutes. To the reaction mixture was added copper(I) bromide (0.37 g) under ice-cooling, and the mixture was stirred for 15 minutes. The resulting reaction mixture was stirred at room temperature for 1 hour, and then warmed to 100° C., and stirred for additional 1 hour. To the reaction mixture was added a saturated potassium carbonate aqueous solution at room temperature, and the mixture was extracted with ethyl acetate. The resulting organic layers were sequentially washed with water and saturated brine, and dried over anhydrous sodium sulfate. The resulting residues were subjected to silica gel chromatography to give the Intermediate compound 21 represented by the following formula (8.22 g).

Intermediate Compound 21

¹H-NMR (CDCl₃) δ: 8.46 (1H, d), 7.88 (1H, td), 7.79-7.76 (1H, m), 7.42-7.39 (1H, m), 7.37-7.32 (2H, m), 4.53 (2H, td).

Preparation Example 16

To a mixture of the Present compound 56 (2.50 g) and NMP (28 mL) were added zinc cyanide (1.33 g) and tetrakistriphenylphosphinepalladium(0) (0.33 g). The resulting reaction mixture was stirred at 90° C. for 4 hours, and then warmed to 180° C., and stirred for 1 hour. To the reaction mixture was added water at room temperature, and the mixture was extracted with 2-methoxy-2-methylpropane. The resulting organic layers were sequentially washed with water and saturated brine, and dried over anhydrous sodium sulfate. The resulting residues were subjected to silica gel chromatography to give the Present compound 59 represented by the following formula (0.10 g).

Present Compound 59

¹H-NMR (CDCl₃) δ: 8.48 (1H, d), 7.60-7.58 (2H, m), 7.54-7.49 (2H, m), 7.37 (1H, dd), 4.54 (2H, t), 2.91 (2H, q), 1.29 (3H, dd).

The compound prepared according to the process described in the Preparation Example 16 and the physical properties thereof are shown below.

Present Compound 60

¹H-NMR (CDCl₃) δ: 8.47 (1H, d), 8.40 (1H, d), 7.97 (1H, dd), 7.59 (1H, d), 7.50 (1H, d), 7.40 (1H, dd), 4.54 (2H, t), 3.54 (2H, q), 1.31 (3H, t).

Preparation Example 17

To a mixture of the Present compound 60 (1.19 g) and water (0.8 mL) was added sulfuric acid (2.2 mL) under ice-cooling. The resulting reaction mixture was stirred at 130° C. for 30 minutes. To the reaction mixture was added 10 M sodium hydroxide at room temperature, and the mixture was extracted with ethyl acetate. The resulting organic layers were sequentially washed with 2 M dilute hydrochloric acid and saturated brine, and dried over anhydrous sodium sulfate. The resulting organic layers were concentrated under reduced pressure to give the Present compound 61 represented by the following formula (1.02 g).

Present Compound 61

¹H-NMR (CDCl₃) δ: 8.49-8.49 (1H, m), 8.39-8.38 (1H, m), 8.25 (1H, dd), 7.59-7.57 (1H, m), 7.51-7.49 (1H, m), 7.38 (1, dd), 4.54 (2H, td), 3.53 (2H, q), 1.30 (3H, t).

Preparation Example 18

A mixture of the Present compound 58 (0.86 g), 1,2,4-triazole (0.38 g), copper(I) iodide (0.35 g), cesium carbonate (3.60 g), 8-hydroxyquinoline (0.21 g), water (1.4 mL), and DMF (12.5 mL) was stirred at 150° C. for 5 hours. To the reaction mixture was added water at room temperature, and the mixture was extracted with 2-methoxy-2-methylpropane. The resulting organic layers were sequentially washed with water and saturated brine, and dried over anhydrous sodium sulfate. The resulting residues were subjected to silica gel chromatography to give the Present compound 67 represented by the following formula (0.08 g).

Present Compound 67

¹H-NMR (CDCl₃) δ: 8.73 (1H, s), 8.47 (1H, d), 8.40 (1H, d), 8.18 (1H, s), 8.09 (1H, dd), 7.63 (1H, d), 7.53 (1H, d), 7.39 (1H, dd), 4.55 (2H, t), 3.54 (2H, q), 1.32 (3H, t).

The compound prepared according to the process described in the Preparation Example 18 and the physical properties thereof are shown below.

Present Compound 70

¹H-NMR (CDCl₃) δ: 8.80 (1H, s), 8.48 (1H, d), 8.41 (1H, d), 8.12 (1H, dd), 7.67 (1H, d), 7.53 (1H, d), 7.40 (1H, dd), 4.55 (2H, t), 3.57 (2H, q), 1.33 (3H, t).

Preparation Example 19

To a mixture of the Present compound 58 (500 mg), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (402 mg), potassium acetate (309 mg), and DMSO (3.5 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (38 mg), and the mixture was stirred at 100° C. for 4.5 hours. To the reaction mixture was added water at room temperature, and the mixture was extracted with 2-methoxy-2-methylpropane. The resulting organic layers were sequentially washed with water and saturated brine, and dried over anhydrous sodium sulfate. The resulting residues were subjected to silica gel chromatography to give the Intermediate compound 27 represented by the following formula (454 mg).

Intermediate Compound 27

¹H-NMR (CDCl₃) δ: 8.56 (1H, d), 8.36 (1H, dd), 8.08 (1H, dd), 7.47 (1H, dd), 7.43 (1H, dd), 7.35 (1H, dd), 4.52 (2H, td), 3.46 (2H, q), 1.37 (12H, s), 1.29 (3H, t).

Preparation Example 20

To a mixture of the Intermediate compound 27 (209 mg), 2-bromopyridine (127 mg), a 2 M sodium carbonate aqueous solution (0.6 mL), and 1,2-dimethoxyethane (1.3 mL) was added tetrakistriphenylphosphinepalladium(0) (46 mg) under nitrogen atmosphere at room temperature. The resulting mixture was stirred at 80° C. for 2 hours. The resulting reaction mixture was allowed to stand to room temperature, and to the mixture was added water, and the mixture was extracted with ethyl acetate. The resulting organic layers were dried over anhydrous sodium sulfate, and the organic layers were concentrated under reduced pressure. The resulting residues were subjected to silica gel chromatography to give the Present compound 68 represented by the following formula (113 mg).

Present Compound 68

¹H-NMR (CDCl₃) δ: 8.76-8.73 (2H, m), 8.42-8.39 (2H, m), 7.89-7.81 (2H, m), 7.57 (1H, d), 7.53 (1H, dd), 7.38 (1H, dd), 7.35-7.31 (1H, m), 4.54 (2H, td), 3.53 (2H, q), 1.32 (3H, t).

The compound prepared according to the process described in the Preparation Example 20 and the physical properties thereof are shown below.

Present Compound 69

¹H-NMR (CDCl₃) δ: 9.01-9.00 (1H, m), 8.79 (1H, d), 8.45 (1H, dd), 8.41-8.39 (1H, m), 8.07 (1H, dd), 8.00 (1H, d), 7.61 (1H, d), 7.55-7.53 (1H, m), 7.39 (1H, dd), 4.55 (2H, t), 3.54 (2H, q), 1.32 (3H, t).

A compound represented by formula (100)

[wherein R³⁰¹, R³⁰², R³⁰³, R⁶⁰¹, R⁶⁰², R¹⁰⁰, and A¹ represent any one combination indicated in the following Table 11 to Table 36.] may be prepared according to any one of the above processes.

TABLE 13 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 79 CF₂HCH₂ H H NH₂ H H H 80 CF₂HCF₂CH₂ H H NH₂ H H H 81 CF₃CF₂CF₂CH₂ H H NH₂ H H H 82 CF₃CFHCF₂CH₂ H H NH₂ H H H 83 CF₂HCH₂ H H NHCH₃ H H H 84 CF₃CF₂CH₂ H H NHCH₃ H H H 85 CF₂HCF₂CH₂ H H NHCH₃ H H H 86 CF₃CF₂CF₂CH₂ H H NHCH₃ H H H 87 CF₃CFHCF₂CH₂ H H NHCH₃ H H H 88 CF₂HCH₂ H H N(CH₃)₂ H H H 89 CF₃CF₂CH₂ H H N(CH₃)₂ H H H 90 CF₂HCF₂CH₂ H H N(CH₃)₂ H H H 91 CF₃CF₂CF₂CH₂ H H N(CH₃)₂ H H H 92 CF₃CFHCF₂CH₂ H H N(CH₃)₂ H H H 93 CF₂HCH₂ H H N(CH₂CH₃)₂ H H H 94 CF₃CF₂CH₂ H H N(CH₂CH₃)₂ H H H 95 CF₂HCF₂CH₂ H H N(CH₂CH₃)₂ H H H 96 CF₃CF₂CF₂CH₂ H H N(CH₂CH₃)₂ H H H 97 CF₃CFHCF₂CH₂ H H N(CH₂CH₃)₂ H H H 98 CF₂HCH₂ H H NHCH₂CF₃ H H H 99 CF₃CF₂CH₂ H H NHCH₂CF₃ H H H 100 CF₂HCF₂CH₂ H H NHCH₂CF₃ H H H 101 CF₃CF₂CF₂CH₂ H H NHCH₂CF₃ H H H 102 CF₃CFHCF₂CH₂ H H NHCH₂CF₃ H H H

TABLE 14 Present com- pound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 103 CF₂HCH₂ H H Cl H H H 104 CF₂HCF₂CH₂ H H Cl H H H 105 CF₃CF₂CF₂CH₂ H H Cl H H H 106 CF₃CFHCF₂CH₂ H H Cl H H H 107 CF₂HCH₂ H Cl H H H H 108 CF₂HCF₂CH₂ H Cl H H H H 109 CF₃CF₂CF₂CH₂ H Cl H H H H 110 CF₃CFHCF₂CH₂ H Cl H H H H 111 CF₂HCH₂ H H OCH₃ H H H 112 CF₂HCF₂CH₂ H H OCH₃ H H H 113 CF₃CF₂CF₂CH₂ H H OCH₃ H H H 114 CF₃CFHCF₂CH₂ H H OCH₃ H H H

TABLE 15 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 115 CF₂HCH₂ H H

H H H 116 CF₃CF₂CH₂ H H

H H H 117 CF₂HCF₂CH₂ H H

H H H 118 CF₃CF₂CF₂CH₂ H H

H H H 119 CF₃CFHCF₂CH₂ H H

H H H 120 CF₂HCH₂ H H

H H H 121 CF₃CF₂CH₂ H H

H H H 122 CF₂HCF₂CH₂ H H

H H H 123 CF₃CF₂CF₂CH₂ H H

H H H 124 CF₃CFHCF₂CH₂ H H

H H H

TABLE 16 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 125 CF₂HCH₂ H H

H H H 126 CF₃CF₂CH₂ H H

H H H 127 CF₂HCF₂CH₂ H H

H H H 128 CF₃CF₂CF₂CH₂ H H

H H H 129 CF₃CFHCF₂CH₂ H H

H H H 130 CF₂HCH₂ H H

H H H 131 CF₃CF₂CH₂ H H

H H H 132 CF₂HCF₂CH₂ H H

H H H 133 CF₃CF₂CF₂CH₂ H H

H H H 134 CF₃CFHCF₂CH₂ H H

H H H

TABLE 17 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 136 CF₂HCH₂ H H

H H H 137 CF₃CF₂CH₂ H H

H H H 138 CF₂HCF₂CH₂ H H

H H H 139 CF₃CF₂CF₂CH₂ H H

H H H 140 CF₃CFHCF₂CH₂ H H

H H H 141 CF₂HCH₂ H H

H H H 142 CF₃CF₂CH₂ H H

H H H 143 CF₂HCF₂CH₂ H H

H H H 144 CF₃CF₂CF₂CH₂ H H

H H H 145 CF₃CFHCF₂CH₂ H H

H H H

TABLE 18 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 146 CF₂HCH₂ H H

H H H 147 CF₃CF₂CH₂ H H

H H H 148 CF₂HCF₂CH₂ H H

H H H 149 CF₃CF₂CF₂CH₂ H H

H H H 150 CF₃CFHCF₂CH₂ H H

H H H 151 CF₂HCH₂ H H

H H H 152 CF₃CF₂CH₂ H H

H H H 153 CF₂HCF₂CH₂ H H

H H H 154 CF₃CF₂CF₂CH₂ H H

H H H 155 CF₃CFHCF₂CH₂ H H

H H H

TABLE 19 Present Compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 156 CF₂HCH₂ H H

H H H 157 CF₃CF₂CH₂ H H

H H H 158 CF₂HCF₂CH₂ H H

H H H 159 CF₃CF₂CF₂CH₂ H H

H H H 160 CF₃CFHCF₂CH₂ H H

H H H 161 CF₂HCH₂ H H

H H H 162 CF₃CF₂CH₂ H H

H H H 163 CF₂HCF₂CH₂ H H

H H H 164 CF₃CF₂CF₂CH₂ H H

H H H 165 CF₃CFHCF₂CH₂ H H

H H H

TABLE 20 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 166 CF₂HCH₂ H H

H H H 167 CF₃CF₂CH₂ H H

H H H 168 CF₂HCF₂CH₂ H H

H H H 169 CF₃CF₂CF₂CH₂ H H

H H H 170 CF₃CFHCF₂CH₂ H H

H H H 171 CF₂HCH₂ H H

H H H 172 CF₃CF₂CH₂ H H

H H H 173 CF₂HCF₂CH₂ H H

H H H 174 CF₃CF₂CF₂CH₂ H H

H H H 175 CF₃CFHCF₂CH₂ H H

H H H

TABLE 21 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 176 CF₂HCH₂ H

H H H H 177 CF₃CF₂CH₂ H

H H H H 178 CF₂HCF₂CH₂ H

H H H H 179 CF₃CF₂CF₂CH₂ H

H H H H 180 CF₃CFHCF₂CH₂ H

H H H H 181 CF₂HCH₂ H

H H H H 182 CF₃CF₂CH₂ H

H H H H 183 CF₂HCF₂CH₂ H

H H H H 184 CF₃CF₂CF₂CH₂ H

H H H H 185 CF₃CFHCF₂CH₂ H

H H H H

TABLE 22 Present Compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 186 CF₂HCH₂ H

H H H H 187 CF₃CF₂CH₂ H

H H H H 188 CF₂HCF₂CH₂ H

H H H H 189 CF₃CF₂CF₂CH₂ H

H H H H 190 CF₃CFHCF₂CH₂ H

H H H H 191 CF₂HCH₂ H

H H H H 192 CF₃CF₂CH₂ H

H H H H 193 CF₂HCF₂CH₂ H

H H H H 194 CF₃CF₂CF₂CH₂ H

H H H H 195 CF₃CFHCF₂CH₂ H

H H H H

TABLE 23 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 196 CF₂HCH₂ H

H H H H 197 CF₃CF₂CH₂ H

H H H H 198 CF₂HCF₂CH₂ H

H H H H 199 CF₃CF₂CF₂CH₂ H

H H H H 200 CF₃CFHCF₂CH₂ H

H H H H 201 CF₂HCH₂ H

H H H H 202 CF₃CF₂CH₂ H

H H H H 203 CF₂HCF₂CH₂ H

H H H H 204 CF₃CF₂CF₂CH₂ H

H H H H 205 CF₃CFHCF₂CH₂ H

H H H H

TABLE 24 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 206 CF₂HCH₂ H

H H H H 207 CF₃CF₂CH₂ H

H H H H 208 CF₂HCF₂CH₂ H

H H H H 209 CF₃CF₂CF₂CH₂ H

H H H H 210 CF₃CFHCF₂CH₂ H

H H H H 211 CF₂HCH₂ H

H H H H 212 CF₃CF₂CH₂ H

H H H H 213 CF₂HCF₂CH₂ H

H H H H 214 CF₃CF₂CF₂CH₂ H

H H H H 215 CF₃CFHCF₂CH₂ H

H H H H

TABLE 25 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 216 CF₂HCH₂ H

H H H H 217 CF₃CF₂CH₂ H

H H H H 218 CF₂HCF₂CH₂ H

H H H H 219 CF₃CF₂CF₂CH₂ H

H H H H 220 CF₃CFHCF₂CH₂ H

H H H H 221 CF₂HCH₂ H

H H H H 222 CF₃CF₂CH₂ H

H H H H 223 CF₂HCF₂CH₂ H

H H H H 224 CF₃CF₂CF₂CH₂ H

H H H H 225 CF₃CFHCF₂CH₂ H

H H H H

TABLE 26 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 226 CF₂HCH₂ H

H H H H 227 CF₃CF₂CH₂ H

H H H H 228 CF₂HCF₂CH₂ H

H H H H 229 CF₃CF₂CF₂CH₂ H

H H H H 230 CF₃CFHCF₂CH₂ H

H H H H 231 CF₂HCH₂ H

H H H H 232 CF₃CF₂CH₂ H

H H H H 233 CF₂HCF₂CH₂ H

H H H H 234 CF₃CF₂CF₂CH₂ H

H H H H 235 CF₃CFHCF₂CH₂ H

H H H H

TABLE 27 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 236 CF₂HCH₂ H

H H H H 237 CF₃CF₂CH₂ H

H H H H 238 CF₂HCF₂CH₂ H

H H H H 239 CF₃CF₂CF₂CH₂ H

H H H H 240 CF₃CFHCF₂CH₂ H

H H H H 241 CF₂HCH₂ H

H H H H 242 CF₃CF₂CH₂ H

H H H H 243 CF₂HCF₂CH₂ H

H H H H 244 CF₃CF₂CF₂CH₂ H

H H H H 245 CF₃CFHCF₂CH₂ H

H H H H

TABLE 28 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 246 CF₂HCH₂ H

H H H H 247 CF₃CF₂CH₂ H

H H H H 248 CF₂HCF₂CH₂ H

H H H H 249 CF₃CF₂CF₂CH₂ H

H H H H 250 CF₃CFHCF₂CH₂ H

H H H H 251 CF₂HCH₂ H

H H H H 252 CF₃CF₂CH₂ H

H H H H 253 CF₂HCF₂CH₂ H

H H H H 254 CF₃CF₂CF₂CH₂ H

H H H H 255 CF₃CFHCF₂CH₂ H

H H H H

TABLE 29 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 256 CF₂HCH₂ H

H H H H 257 CF₃CF₂CH₂ H

H H H H 258 CF₂HCF₂CH₂ H

H H H H 259 CF₃CF₂CF₂CH₂ H

H H H H 260 CF₃CFHCF₂CH₂ H

H H H H 261 CF₂HCH₂ H

H H H H 262 CF₃CF₂CH₂ H

H H H H 263 CF₂HCF₂CH₂ H

H H H H 264 CF₃CF₂CF₂CH₂ H

H H H H 265 CF₃CFHCF₂CH₂ H

H H H H

TABLE 30 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 266 CF₂HCH₂ H

H H H H 267 CF₂HCF₂CH₂ H

H H H H 268 CF₃CF₂CF₂CH₂ H

H H H H 269 CF₃CFHCF₂CH₂ H

H H H H 270 CF₂HCH₂ H

H H H H 271 CF₃CF₂CH₂ H

H H H H 272 CF₂HCF₂CH₂ H

H H H H 273 CF₃CF₂CF₂CH₂ H

H H H H 274 CF₃CFHCF₂CH₂ H

H H H H

TABLE 31 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 276 CF₂HCH₂ H

H H H H 277 CF₃CF₂CH₂ H

H H H H 278 CF₂HCF₂CH₂ H

H H H H 279 CF₃CF₂CF₂CH₂ H

H H H H 280 CF₃CFHCF₂CH₂ H

H H H H 281 CF₂HCH₂ H

H H H H 282 CF₃CF₂CH₂ H

H H H H 283 CF₂HCF₂CH₂ H

H H H H 284 CF₃CF₂CF₂CH₂ H

H H H H 285 CF₃CFHCF₂CH₂ H

H H H H

TABLE 32 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 286 CF₂HCH₂ H

H H H H 287 CF₃CF₂CH₂ H

H H H H 288 CF₂HCF₂CH₂ H

H H H H 289 CF₃CF₂CF₂CH₂ H

H H H H 290 CF₃CFHCF₂CH₂ H

H H H H 291 CF₂HCH₂ H

H H H H 292 CF₂HCF₂CH₂ H

H H H H 293 CF₃CF₂CF₂CH₂ H

H H H H 294 CF₃CFHCF₂CH₂ H

H H H H

TABLE 33 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 296 CF₂HCH₂ H

H H H H 297 CF₃CF₂CH₂ H

H H H H 298 CF₂HCF₂CH₂ H

H H H H 299 CF₃CF₂CF₂CH₂ H

H H H H 300 CF₃CFHCF₂CH₂ H

H H H H 301 CF₂HCH₂ H

H H H H 302 CF₃CF₂CH₂ H

H H H H 303 CF₂HCF₂CH₂ H

H H H H 304 CF₃CF₂CF₂CH₂ H

H H H H 305 CF₃CFHCF₂CH₂ H

H H H H

TABLE 34 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 306 CF₂HCH₂ H

H H H H 307 CF₃CF₂CH₂ H

H H H H 308 CF₂HCF₂CH₂ H

H H H H 309 CF₃CF₂CF₂CH₂ H

H H H H 310 CF₃CFHCF₂CH₂ H

H H H H

TABLE 35 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 311 CF₂HCH₂ H OCH₃ H H H H 312 CF₂HCF₂CH₂ H OCH₃ H H H H 313 CF₃CF₂CF₂CH₂ H OCH₃ H H H H 314 CF₃CFHCF₂CH₂ H OCH₃ H H H H 315 CF₂HCH₂ H OCH₂CH₃ H H H H 316 CF₃CF₂CH₂ H OCH₂CH₃ H H H H 317 CF₂HCF₂CH₂ H OCH₂CH₃ H H H H 318 CF₃CF₂CF₂CH₂ H OCH₂CH₃ H H H H 319 CF₃CFHCF₂CH₂ H OCH₂CH₃ H H H H 320 CF₂HCH₂ H OCH(CH₃)₂ H H H H 321 CF₃CF₂CH₂ H OCH(CH₃)₂ H H H H 322 CF₂HCF₂CH₂ H OCH(CH₃)₂ H H H H 323 CF₃CF₂CF₂CH₂ H OCH(CH₃)₂ H H H H 324 CF₃CFHCF₂CH₂ H OCH(CH₃)₂ H H H H 325 CF₂HCH₂ H OCH₂CH₂N(CH₃)₂ H H H H 326 CF₃CF₂CH₂ H OCH₂CH₂N(CH₃)₂ H H H H 327 CF₂HCF₂CH₂ H OCH₂CH₂N(CH₃)₂ H H H H 328 CF₃CF₂CF₂CH₂ H OCH₂CH₂N(CH₃)₂ H H H H 329 CF₃CFHCF₂CH₂ H OCH₂CH₂N(CH₃)₂ H H H H 330 CF₂HCH₂ H OCH₂CF₃ H H H H 331 CF₃CF₂CH₂ H OCH₂CF₃ H H H H 332 CF₂HCF₂CH₂ H OCH₂CF₃ H H H H 333 CF₃CF₂CF₂CH₂ H OCH₂CF₃ H H H H 334 CF₃CFHCF₂CH₂ H OCH₂CF₃ H H H H

TABLE 36 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 335 CF₂HCH₂ H OCH₂CF₃ H H H H 336 CF₃CF₂CH₂ H OCH₂CF₃ H H H H 337 CF₂HCF₂CH₂ H OCH₂CF₃ H H H H 338 CF₃CF₂CF₂CH₂ H OCH₂CF₃ H H H H 339 CF₃CFHCF₂CH₂ H OCH₂CF₃ H H H H 340 CF₂HCH₂ H OCH₂CF₂CF₂H H H H H 341 CF₃CF₂CH₂ H OCH₂CF₂CF₂H H H H H 342 CF₂HCF₂CH₂ H OCH₂CF₂CF₂H H H H H 343 CF₃CF₂CF₂CH₂ H OCH₂CF₂CF₂H H H H H 344 CF₃CFHCF₂CH₂ H OCH₂CF₂CF₂H H H H H 345 CF₂HCH₂ H OCH₂CF₂CF₃ H H H H 346 CF₃CF₂CH₂ H OCH₂CF₂CF₃ H H H H 347 CF₂HCF₂CH₂ H OCH₂CF₂CF₃ H H H H 348 CF₃CF₂CF₂CH₂ H OCH₂CF₂CF₃ H H H H 349 CF₃CFHCF₂CH₂ H OCH₂CF₂CF₃ H H H H 350 CF₂HCH₂ H NHC(O)CH₃ H H H H 351 CF₃CF₂CH₂ H NHC(O)CH₃ H H H H 352 CF₂HCF₂CH₂ H NHC(O)CH₃ H H H H 353 CF₃CF₂CF₂CH₂ H NHC(O)CH₃ H H H H 354 CF₃CFHCF₂CH₂ H NHC(O)CH₃ H H H H 355 CF₂HCH₂ H NHC(O)CH₂CH₃ H H H H 356 CF₃CF₂CH₂ H NHC(O)CH₂CH₃ H H H H 357 CF₂HCF₂CH₂ H NHC(O)CH₂CH₃ H H H H 358 CF₃CF₂CF₂CH₂ H NHC(O)CH₂CH₃ H H H H 359 CF₃CFHCF₂CH₂ H NHC(O)CH₂CH₃ H H H H

TABLE 37 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 360 CF₂HCH₂ H

H H H H 361 CF₂HCF₂CH₂ H

H H H H 362 CF₃CF₂CF₂CH₂ H

H H H H 363 CF₃CFHCF₂CH₂ H

H H H H 364 CF₂HCH₂ H

H H H H 365 CF₃CF₂CH₂ H

H H H H 366 CF₂HCF₂CH₂ H

H H H H 367 CF₃CF₂CF₂CH₂ H

H H H H 368 CF₃CFHCF₂CH₂ H

H H H H

TABLE 38 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 369 CF₂HCH₂ H NHC(O)OCH₃ H H H H 370 CF₃CF₂CH₂ H NHC(O)OCH₃ H H H H 371 CF₂HCF₂CH₂ H NHC(O)OCH₃ H H H H 372 CF₃CF₂CF₂CH₂ H NHC(O)OCH₃ H H H H 373 CF₃CFHCF₂CH₂ H NHC(O)OCH₃ H H H H 374 CF₂HCH₂ H NHC(O)OCH₂CH₃ H H H H 375 CF₃CF₂CH₂ H NHC(O)OCH₂CH₃ H H H H 376 CF₂HCF₂CH₂ H NHC(O)OCH₂CH₃ H H H H 377 CF₃CF₂CF₂CH₂ H NHC(O)OCH₂CH₃ H H H H 378 CF₃CFHCF₂CH₂ H NHC(O)OCH₂CH₃ H H H H 379 CF₂HCH₂ H OCH₂CH₂CH₃ H H H H 380 CF₃CF₂CH₂ H OCH₂CH₂CH₃ H H H H 381 CF₂HCF₂CH₂ H OCH₂CH₂CH₃ H H H H 382 CF₃CF₂CF₂CH₂ H OCH₂CH₂CH₃ H H H H 383 CF₃CFHCF₂CH₂ H OCH₂CH₂CH₃ H H H H

Next, the Formulation examples of the Present compound are shown below. The “part(s)” represents “part(s) by weight” unless otherwise specified.

Formulation Example 1

Any one of the Present compounds 1 to 383 (10 parts) is mixed with a mixture of xylene (35 parts) and DMF (35 parts), and then polyoxyethylene styryl phenyl ether (14 parts) and calcium dodecylbenzene sulfonate (6 parts) are added thereto, followed by mixing them to obtain each formulation.

Formulation Example 2

Sodium lauryl sulfate (4 parts), calcium lignin sulfonate (2 parts), synthetic hydrated silicon oxide fine powder (20 parts), and diatomaceous earth (54 parts) are mixed, and further any one of the Present compounds 1 to 383 (20 parts) is added thereto, followed by mixing them to obtain each wettable powder.

Formulation Example 3

To any one of the Present compounds 1 to 383 (2 parts) are added synthetic hydrated silicon oxide fine powder (1 part), calcium lignin sulfonate (2 parts), bentonite (30 parts), and kaolin clay (65 parts), followed by mixing them to obtain a mixture. To the mixture is then added an appropriate amount of water, and the resulting mixture is additionally stirred, and subjected to granulation with a granulator and forced-air drying to obtain each granular formulation.

Formulation Example 4

Any one of the Present compounds 1 to 383 (1 part) is mixed with an appropriate amount of acetone, and then synthetic hydrated silicon oxide fine powder (5 parts), isopropyl acid phosphate (0.3 parts), and kaolin clay (93.7 parts) are added thereto, followed by mixing with stirring thoroughly and removal of acetone from the mixture by evaporation to obtain each powder formulation.

Formulation Example 5

A mixture of polyoxyethylene alkyl ether sulfate ammonium salt and white carbon (weight ratio of 1:1) (35 parts), any one of the Present compounds 1 to 383 (10 parts), and water (55 parts) are mixed, followed by finely grounding by a wet grinding method to obtain each flowable formulation.

Formulation Example 6

Any one of the Present compounds 1 to 383 (0.1 part) is mixed with a mixture of xylene (5 parts) and trichloroethane (5 parts), and the resulting mixture is then mixed with kerosene (89.9 parts) to obtain each oil solution.

Formulation Example 7

Any one of the Present compounds 1 to 383 (10 mg) is mixed with acetone (0.5 mL), and the solution is added dropwise to a solid feed powder for an animal (solid feed powder for rearing and breeding CE-2, manufactured by CLEA Japan, Inc.) (5 g), followed by mixing the resulting mixture uniformly, and then by drying it by evaporation of acetone to obtain each poison bait.

Formulation Example 8

Any one of the Present compounds 1 to 383 (0.1 part) and Neothiozole (manufactured by Chuo Kasei Co., Ltd.) (49.9 parts) are placed into an aerosol can. After mounting an aerosol valve, dimethyl ether (25 parts) and LPG (25 parts) are filled, followed by shaking and further mounting an actuator to obtain each oily aerosol.

Formulation Example 9

A mixture of any one of the Present compounds 1 to 383 (0.6 parts), BHT (2,6-di-tert-butyl-4-methylphenol) (0.01 part), xylene (5 parts), deodorized kerosene (3.39 parts), and an emulsifier {Rheodol MO-60 (manufactured by Kao Corporation)} (1 part), and distilled water (50 parts) are filled into an aerosol container, and a valve part is attached. Then, a propellant (LPG) (40 parts) is filled therein through the valve under pressure to obtain each aqueous aerosol.

Formulation Example 10

Any one of the Present compounds 1 to 383 (0.1 g) is mixed with propylene glycol (2 mL), and the resulting solution is impregnated into a ceramic plate having a size of 4.0 cm×4.0 cm and a thickness of 1.2 cm to obtain each thermal fumigant.

Formulation Example 11

Any one of the Present compounds 1 to 383 (5 parts) and ethylene-methyl methacrylate copolymer (the ratio of the methyl methacrylate in the copolymer:10% by weight, Acryft (registered trademark) WD 301, manufactured by Sumitomo Chemical Co. Ltd.) (95 parts) are melted and kneaded with a closed type pressure kneader (manufactured by Moriyama Co., Ltd.), and the resulting kneaded product is extruded from an extrusion molding machine through a molding die to obtain each rod-shaped molded product having a length of 15 cm and a diameter of 3 mm.

Formulation Example 12

Any one of the Present compounds 1 to 383 (5 parts) and flexible vinyl chloride resin (95 parts) are melted and kneaded with a closed type pressure kneader (manufactured by Moriyama Co., Ltd.), and the resulting kneaded product is extruded from an extrusion molding machine through a molding die to obtain each rod-shaped molded product having a length of 15 cm and a diameter of 3 mm.

Formulation Example 13

Any one of the Present compounds 1 to 383 (100 mg), lactose (68.75 mg), corn starch (237.5 mg), microcrystalline cellulose (43.75 mg), polyvinylpyrrolidone (18.75 mg), sodium carboxymethyl starch (28.75 mg), and magnesium stearate (2.5 mg) are mixed, and the resulting mixture is compressed to an appropriate size to obtain each tablet.

Formulation Example 14

Any one of the Present compounds 1 to 383 (25 mg), lactose (60 mg), corn starch (25 mg), carmellose calcium (6 mg), and an appropriate amount of 5% hydroxypropyl methylcellulose are mixed, and the resulting mixture is filled into a hard shell gelatin capsule or a hydroxypropyl methylcellulose capsule to obtain each capsule.

Formulation Example 15

To any one of the Present compounds 1 to 383 (100 mg), fumaric acid (500 mg), sodium chloride (2,000 mg), methylparaben (150 mg), propylparaben (50 mg), granulated sugar (25,000 mg), sorbitol (70% solution) (13,000 mg), Veegum K (manufactured by Vanderbilt Co.) (100 mg), perfume (35 mg), and a coloring agent (500 mg) is added distilled water so that the final volume is set to be 100 mL, followed by mixing them to obtain each suspension for oral administration.

Formulation Example 16

Any one of the Present compounds 1 to 383 (5% by weight) is mixed with an emulsifier (5% by weight), benzyl alcohol (3% by weight), and propylene glycol (30% by weight), and phosphate buffer is added thereto so that the pH of the solution is set to be 6.0 to 6.5, and then water is added thereto as the rest parts to obtain each solution for oral administration.

Formulation Example 17

To a mixture of fractional distillated palm oil (57% by weight) and polysorbate 85 (3% by weight) is added aluminum distearate (5% by weight), and the mixture is dispersed by heating. The resulting mixture is cooled to room temperature, and saccharin (25% by weight) is dispersed in the oil vehicle. Any one of the Present compounds 1 to 383 (10% by weight) is divided thereto to obtain each paste formulation for oral administration.

Formulation Example 18

Any one of the Present compounds 1 to 383 (5% by weight) is mixed with a limestone filler (95% by weight), followed by a wet granulation of the resulting mixture to obtain each granule for oral administration.

Formulation Example 19

Any one of the Present compounds 1 to 383 (5 parts) is mixed with diethylene glycol monoethyl ether (80 parts), and propylene carbonate (15 parts) is added thereto, and the resulting mixture is mixed to obtain each spot-on solution.

Formulation Example 20

Any one of the Present compounds 1 to 383 (10 parts) is mixed with diethylene glycol monoethyl ether (70 parts), and 2-octyldodecanol (20 parts) is added thereto, and the resulting mixture is mixed to obtain each pour-on solution.

Formulation Example 21

To any one of the Present compounds 1 to 383 (0.5 parts) are added Nikkol (registered trademark) TEALS-42 (manufactured by Nikko Chemicals Co., Ltd.: a 42% triethanolamine lauryl sulfate aqueous solution) (60 parts) and propylene glycol (20 parts), and the resulting mixture is mixed with stirring thoroughly to obtain a homogeneous solution, and water (19.5 parts) is then added thereto and the resulting mixture is further mixed with stirring thoroughly to obtain each homogeneous solution of shampoo formulation.

Formulation Example 22

Any one of the Present compounds 1 to 383 (0.15% by weight), animal feed (95% by weight), and a mixture (4.85% by weight) consisting of dibasic calcium phosphate, diatomaceous earth, Aerosil, and carbonate (or chalk) are mixed with stirring thoroughly to obtain each premix for animal feed.

Formulation Example 23

Any one of the Present compounds 1 to 383 (7.2 g) and Hosco (registered trademark) S-55 (manufactured by Maruishi Pharmaceuticals) (92.8 g) are mixed at 100° C., and the resulting mixture is poured into a suppository mold, followed by performing a cooling solidification to obtain each suppository.

Next, Test examples are used to show efficacies of the Present compounds on controlling harmful arthropods. In the following Test examples, the tests were carried out at 25° C.

Test Example 1

Each test compound is formulated according to the process described in the Formulation example 5 to obtain each formulation, and water containing a spreader (0.03% by volume) is added thereto to prepare a diluted solution containing a prescribed concentration of each test compound.

Cucumber (Cucumis sativus) seedlings (on the developmental stage of the second true leaf) are planted in a plastic cup and approximately 30 heads of cotton aphid (Aphis gossypii) (all stages of life) are released onto the cucumber seedlings. After 1 day, each of said diluted solutions is sprayed into the seedlings in a ratio of 10 mL/seedling. After additional 5 days, the number of the surviving insects is examined and the controlling value is calculated by the following equation. Controlling value (%)={1−(Cb×Tai)/(Cai×Tb)}×100 wherein the symbols in the formula represent the following meanings.

Cb: Number of the test insects in untreated group;

Cai: Number of the surviving insects at the time of the investigation in untreated group;

Tb: Number of the test insects in treated group;

Tai: Number of the surviving insects at the time of the investigation in treated group;

Here the “untreated group” represents a group where a similar treatment procedure to that of the treated group except not using each test compound is done.

The results of the test that was carried out according to the Test example 1 are shown below.

When the prescribed concentration was 500 ppm, each of the following Present compounds used as a test compound showed 90% or greater as the controlling value.

Present compound number: 1, 2, 3, 5, 6, 7, 8, 9, 11, 13, 14, 21, 22, 23, 25, 28, 31, 32, 33, 34, 36, 37, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 58, 57, 59, 60, 61, 62, 63, 64, 65, 66, 67, and 68

The results of the test that was carried out according to the Test example 1 are shown below.

When the prescribed concentration was 200 ppm, each of the following Present compounds used as a test compound showed 90% or greater as the controlling value.

Present compound number: 1, 2, 5, 6, 8, 11, 44, 46, 52, 56, 58, 59, 60, 61, 62, 64, 65, 66, 67, and 68

Test Example 2

Each test compound is formulated according to the process described in the Formulation example 5 to obtain each formulation, and water is added thereto to prepare a diluted solution containing a prescribed concentration of each test compound.

Cucumber seedlings (on the developmental stage of the second true leaf) are planted in a plastic cup, and each of the diluted solutions is irrigated into the plant foot in a ratio of 5 mL/seedling. After 7 days, approximately 30 heads of cotton aphid (Aphis gossypii) (all stages of life) are inoculated onto the leaves of the seedlings. After additional 6 days, the number of the surviving insects is examined and the controlling value is calculated by the following equation. Controlling value (%)={1−(Cb×Tai)/(Cai×Tb)}×100 wherein the symbols in the formula represent the following meanings.

Cb: Number of the test insects in untreated group;

Cai: Number of the surviving insects at the time of the investigation in untreated group;

Tb: Number of the test insects in treated group;

Tai: Number of the surviving insects at the time of the investigation in treated group;

Here the “untreated group” represents a group where a similar treatment procedure to that of the treated group except not using each test compound is done.

The results of the test that was carried out according to the Test example 2 are shown below.

When the prescribed concentration was 200 ppm, each of the following Present compounds used as a test compound showed 90% or greater as the controlling value.

Present compound number: 60, 66, and 67

Test Example 3

Each test compound is formulated according to the process described in the Formulation example 5 to obtain each formulation, and water containing a spreader (0.03% by volume) is added thereto to prepare a diluted solution containing a prescribed concentration of each test compound.

Rice (Oryza sativa) seedlings (on the developmental stage of the second true leaf) are planted in a plastic cup, and each of the diluted solutions is sprayed into the seedlings in a ratio of 10 mL/seedling. Thereafter, 20 heads of the 3rd instar larvae of brown planthopper (Nilaparvata lugens) are released onto the rice seedlings. After 6 days, the number of the surviving insects is examined and the mortality of insects is calculated by the following equation. Mortality of insects (%)={1−Number of surviving insects/20}×100

The results of the test that was carried out according to the Test example 3 are shown below.

When the prescribed concentration was 500 ppm, each of the following Present compounds used as a test compound showed 90% or greater as the mortality of insects. Present compound number: 1, 6, 8, 25, 28, 47, and 64

Test Example 4

Each test compound is formulated according to the process described in the Formulation example 5 to obtain each formulation, and water is added thereto to prepare a diluted solution containing a prescribed concentration of each test compound.

Each of the diluted solutions (5 mL) is added to a plastic cup, and therein is installed rice seedlings (on the developmental stage of the second true leaf) planted in a plastic cup having a hole in the bottom. After 7 days, 20 heads of the 3rd instar larvae of brown planthopper (Nilaparvata lugens) are released onto the rice seedlings. After additional 6 days, the number of the surviving insects is examined and the mortality of insects is calculated by the following equation. Mortality of insects (%)={1−Number of surviving insects/20}×100

Test Example 5

Each test compound is formulated according to the process described in the Formulation example 5 to obtain each formulation, and water is added thereto to prepare a diluted solution containing a prescribed concentration of each test compound.

An artificial diet (Insecta LF, manufactured by Nosan Corporation) (7.7 g) is placed in a plastic cup, and each of the diluted solutions (2 mL) is irrigated thereto. Five (5) heads of the 4th instar larvae of tobacco cutworm (Spodoptera litura) are released onto the artificial diet, and the cup is covered with a lid. After 5 days, the number of the surviving insects is counted, and the mortality of insects is calculated by the following equation. Mortality of insects (%)=(1−Number of surviving insects/5)×100

The results of the test that was carried out according to the Test example 5 are shown below.

When the prescribed concentration was 500 ppm, each of the following Present compounds used as a test compound showed 80% or greater as the mortality of insects. Present compound number: 7, 8, 9, 11, 13, 14, 22, 23, 41, 47, 48, 49, 54, 56, 57, 58, 67, 68, and 69

Test Example 6

Each test compound is formulated according to the process described in the Formulation example 5 to obtain each formulation, and water containing a spreader (0.03% by volume) is added thereto to prepare a diluted solution containing a prescribed concentration of each test compound.

Cabbage (Brassicae oleracea) seedlings (on the developmental stage of the second to third true leaf) are planted in a plastic cup, and each of the diluted solutions is sprayed into the seedlings in a ratio of 20 mL/seedling. Thereafter, the stem and leaf of the seedling are cut out, and placed into a plastic cup lined with a filter paper. Five (5) heads of the 2nd instar larvae of cabbage moth (Plutella xylostella) are released into the cup, and the cup is covered with a lid. After 5 days, the number of the surviving insects is counted, and the mortality of insects is calculated by the following equation. Mortality %=(1−Number of surviving insects/5)×100

The results of the test that was carried out according to the Test example 6 are shown below.

When the prescribed concentration was 500 ppm, each of the following Present compounds used as a test compound showed 80% or greater as the mortality of insects. Present compound number: 1, 2, 3, 5, 6, 7, 8, 9, 11, 13, 14, 18, 19, 20, 21, 22, 23, 25, 26, 27, 28, 32, 33, 34, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 56, 55, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, and 69

Test Example 7

Each test compound is formulated according to the process described in the Formulation example 5 to obtain each formulation, and water containing a spreader (0.03% by volume) is added thereto to prepare a diluted solution containing a prescribed concentration of each test compound.

Cabbage seedlings (on the developmental stage of the third to fourth true leaf) are planted in a plastic cup, and each of the diluted solutions is sprayed into the seedlings in a ratio of 20 mL/seedling. Thereafter, 10 heads of the 3rd instar larvae of cabbage moth (Plutella xylostella) are released into the cabbage seedlings, and held in a plastic container covered with a net. After 5 days, the number of the surviving insects is counted, and the mortality of insects is calculated by the following equation. Mortality %=(1−Number of surviving insects/10)×100

The results of the test that was carried out according to the Test example 7 are shown below.

When the prescribed concentration was 200 ppm, each of the following Present compounds used as a test compound showed 90% or greater as the mortality of insects.

Present compound number: 2, 5, 6, 7, 8, 9, 11, 18, 27, 32, 33, 34, 32, 33, 34, 41, 47, 48, 49, 55, 56, 57, 58, 59, 60, 62, 63, 64, 65, 66, 67, 68, 69, and 70

Test Example 8

Each test compound is dissolved into a mixed solution (50 μL) of polyoxyethylene sorbitan mono-cocoate:acetone (at a volume ratio of polyoxyethylene sorbitan mono-cocoate:acetone=5:95) per 1 mg of the test compound, and water containing a spreader (0.03% by volume) is added thereto to prepare a diluted solution containing a prescribed concentration of each test compound.

Seeds of corns (Zea mays) are inoculated onto a tray lined with wet Kimwipes. After the corns are grown for 5 days, the entire seedlings of the corns are immersed into each of the diluted solutions for 30 seconds. Thereafter, two seedlings are placed into each plastic petri dish (diameter: 90 mm), and 10 heads of the 2nd instar larvae of western corn rootworm (Diabrotica virgifera virgifera) are released into the dish, and the dish is covered with a lid. After 5 days, the number of the dead insects is counted, and the mortality of insects is calculated by the following equation. Mortality of insects (%)=(Number of dead insects/10)×100

The results of the test that was carried out according to the Test example 8 are shown below.

When the prescribed concentration was 500 ppm, each of the following Present compounds used as a test compound showed 80% or greater as the mortality of insects.

Present compound number: 1, 2, 3, 5, 6, 9, 11, 20, 26, 27, 31, 32, 33, 34, 41, 42, 48, 49, 56, 57, 58, 59, 60, and 64

Test Example 9

Each test compound is dissolved into a mixed solution (10 μL) of xylene, DMF, and a surfactant (at a volume ratio of xylene:DMF:surfactant=4:4:1) per 1 mg of the test compound, and water containing a spreader (0.03% by volume) is added thereto to prepare a diluted solution containing a prescribed concentration of each test compound.

Cucumber seedlings (on the developmental stage of the second to third true leaf) are planted in a plastic cup, and each of the diluted solutions is sprayed into the seedlings in the ratio of 10 mL/seedling. Thereafter, the second leaves are cut out and placed into a plastic cup, and 10 heads of the 2nd instar larvae of cucurbit leaf beetle (Aulacophora femoralis) are released into the cup, and the cup is covered with a lid. After 5 days, the number of the dead insects is counted, and the mortality of insects is calculated by the following equation. Mortality of insects (%)=(Number of dead insects/10)×100

The results of the test that was carried out according to the Test example 9 are shown below.

When the prescribed concentration was 50 ppm, each of the following Present compounds used as a test compound showed 80% or greater as the mortality of insects. Present compound number: 7, 8, and 9

Test Example 10

Each test compound is formulated according to the process described in the Formulation example 5 to obtain each formulation, and water is added thereto to prepare a diluted solution containing a prescribed concentration of each test compound.

A bottom of a plastic cup having a diameter of 5.5 cm is lined with the same size of a filter paper, and each of the diluted solutions (0.7 mL) is added dropwise on the filter paper, and sucrose (30 mg) is homogeneously placed into the plastic cup as a bait. Ten (10) heads of female adult housefly (Musca domestica) are released into the plastic cup, and the cup is covered with a lid. After 24 hours, life or death of the housefly is examined and the mortality of insects is calculated by the following equation. Mortality of insects (%)=(Number of dead insects/Number of test insects)×100

The results of the test that was carried out according to the Test example 10 are shown below.

When the prescribed concentration was 500 ppm, each of the following Present compounds used as a test compound showed 100% or greater as the mortality of insects. Present compound number: 5, 6, 13, 14, 32, 66, and 67

INDUSTRIAL APPLICABILITY

The Present compounds have excellent control efficacies against harmful arthropods. 

The invention claimed is:
 1. A compound represented by formula (I) or an N-oxide thereof:

wherein: R¹ represents a C2-C10 chain hydrocarbon group having one or more halogen atoms, a (C1-C5 alkoxy)C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfanyl)C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfinyl)C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfonyl)C2-C5 alkyl group having one or more halogen atoms, a (C3-C7 cycloalkyl)C1-C3 alkyl group having one or more substituents selected from Group G, or a C3-C7 cycloalkyl group having one or more substituents selected from Group G; R² represents a C1-C6 alkyl group optionally having one or more halogen atoms, a cyclopropylmethyl group, or a cyclopropyl group; q represents 0, 1, 2, 3, or 4; R³ represents a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group B, a phenyl group optionally having one or more substituents selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, a OR¹², a NR¹¹R¹², a NR^(11a)R^(12a), a NR²⁹NR¹¹R¹², a NR²⁹OR¹¹, a NR¹¹C(O)R¹³, a NR²⁹NR¹¹C(O)R¹³, a NR¹¹C(O)OR¹⁴, a NR²⁹NR¹¹C(O)OR¹⁴, a NR¹¹C(O)NR¹⁵R¹⁶, a NR²⁴NR¹¹C(O)NR¹⁵R¹⁶, a N═CHNR¹⁵R¹⁶, a N═S(O)_(x)R¹⁵R¹⁶, a S(O)_(y)R¹⁵, a SF₅, a C(O)OR¹⁷, a C(O)NR¹¹R¹², a cyano group, a nitro group, or a halogen atom, wherein when q represents 2 or 3, two or three R³ may be identical to or different from each other; p represents 0, 1, 2, or 3; R⁶ represents a C1-C6 alkyl group optionally having one or more halogen atoms, a OR¹⁸, a NR¹⁸R¹⁹, a cyano group, a nitro group, or a halogen atom, wherein when p represents 2, two R⁶ may be identical to or different from each other; R¹¹, R¹⁷, R¹⁸, R¹⁹, R²⁴, and R²⁹ represent each independently a hydrogen atom or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms; R¹² represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkyl group having one substituent selected from Group F, or a S(O)₂R²³; R²³ represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or a phenyl group optionally having one or more substituents selected from Group D; R^(11a) and R^(12a) are combined with the nitrogen atom to which they are attached to represent a 3-7 membered nonaromatic heterocyclic group optionally having one or more substituents selected from Group E, wherein the 3-7 membered nonaromatic heterocyclic group represents an aziridine ring, an azetidine ring, a pyrrolidine ring, an imidazoline ring, an imidazolidine ring, a piperidine ring, a tetrahydropyrimidine ring, a hexahydropyrimidine ring, a piperazine ring, an azepane ring, an oxazolidine ring, an isoxazolidine ring, a 1,3-oxazinane ring, a morpholine ring, a 1,4-oxazepane ring, a thiazolidine ring, an isothiazolidine ring, a 1,3-thiazinane ring, a thiomorpholine ring, or a 1,4-thiazepane ring; R¹³ represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally having one or more halogen atoms, a phenyl group optionally having one or more substituents selected from Group D, or a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituents selected from Group D; R¹⁴ represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally having one or more halogen atoms, or a phenyl C1-C3 alkyl group, wherein the phenyl moiety in the phenyl C1-C3 alkyl group may optionally have one or more substituents selected from Group D; R¹⁵ and R¹⁶ represent each independently a C1-C6 alkyl group optionally having one or more halogen atoms; n and y represent each independently 0, 1, or 2; x represents 0 or 1; Group B is selected from the group consisting of a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, a cyano group, a hydroxy group, and a halogen atom; Group C is selected from the group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, and a halogen atom; Group D is selected from the group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a hydroxy group, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, a sulfanyl group, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, an amino group, a NHR²¹, a NR²¹R²², a C(O)R²¹ group, a OC(O)R²¹ group, a C(O)OR²¹ group, a cyano group, a nitro group, and a halogen atom, wherein R²¹ and R²² represent each independently a C1-C6 alkyl group optionally having one or more halogen atoms; Group E is selected from the group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, a halogen atom, an oxo group, a hydroxy group, a cyano group, and a nitro group; Group F is selected from the group consisting of a C1-C6 alkoxy group optionally having one or more halogen atoms, an amino group, a NHR²¹, a NR²¹R²², a cyano group, a phenyl group optionally having one or more substituents selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and a 3-7 membered nonaromatic heterocyclic group optionally having one or more substituents selected from Group C; and Group G is selected from the group consisting of a halogen atom and a C1-C6 haloalkyl group.
 2. The compound according to claim 1, wherein q represents 0, 1, or 2; and R³ represents a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group B, a phenyl group optionally having one or more substituents selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, a OR¹², a NR¹¹R¹², a NR^(11a)R^(12a), a NR¹¹C(O)R¹³, a NR²⁹NR¹¹C(O)R¹³, a NR¹¹C(O)OR¹⁴, a C(O)OR¹⁷, a C(O)NR¹¹R¹², a cyano group, a nitro group, or a halogen atom.
 3. The compound according to claim 1, wherein q represents 0, 1, or 2; R³ represents a C1-C6 alkyl group having one or more halogen atoms, a OR¹², or a halogen atom; and R¹² represents a hydrogen atom or a C1-C3 alkyl group optionally having one or more halogen atoms.
 4. The compound according to claim 1, wherein p represents 0 or 1; and R⁶ represents a C1-C6 alkyl group optionally having one or more halogen atoms, or a halogen atom.
 5. The compound according to claim 1, wherein p represents
 0. 6. The compound according to claim 1, wherein R¹ represents a C2-C10 haloalkyl group.
 7. The compound according to claim 1, wherein R¹ represents a C3-C5 alkyl group having four or more fluorine atoms.
 8. The compound according to claim 1, wherein R² represents a C1-C6 alkyl group optionally having one or more halogen atoms.
 9. The compound according to claim 1, wherein R² represents an ethyl group.
 10. The compound according to claim 1, wherein R¹ represents a C2-C10 haloalkyl group; R² represents an ethyl group; q represents 0 or 1; R³ represents a C1-C6 alkyl group optionally having one or more halogen atoms, or a halogen atom; p represents 0 or 1; and R⁶ represents a C1-C6 alkyl group optionally having one or more halogen atoms, or a halogen atom.
 11. The compound according to claim 1, wherein R¹ represents a C3-C5 alkyl group having four or more fluorine atoms; R² represents an ethyl group; q represents 0 or 1; R³ represents a C1-C6 alkyl group optionally having one or more halogen atoms, or a halogen atom; and p represents
 0. 12. A composition for controlling a harmful arthropod comprising the compound according to claim 1 and an inert carrier.
 13. A method for controlling a harmful arthropod which comprises applying an effective amount of the compound according to claim 1 to a harmful arthropod or a habitat where a harmful arthropod lives. 